Environmentally Benign and Scalable Preparation of Diethyl Furoxan-3,4-dicarboxylate Using Silver Carbonate as a Nitrile Oxide Generator

Zhang, Mao-Xi; DeHope, Alan J.; Pagoria, Philip. F.

doi:10.1021/acs.oprd.9b00228

Title: Environmentally Benign and Scalable Preparation of Diethyl Furoxan-3,4-dicarboxylate Using Silver Carbonate as a Nitrile Oxide Generator

Abstract

Diethyl furoxan-3,4-dicarboxylate (1) is a starting material for many heterocyclic compounds containing furoxan and furazan rings. Usually, furoxan 1 was prepared via a dimerization of corresponding nitrile oxide generated either by treatment of ethyl 2-chloro-2-(hydroxyimino)-acetate (2) with triethylamine or by nitration or conversion of α-activated ethyl acetate with acetyl nitrate in acetic acid or other catalytic reagents. Both methods are suitable for small-scale but suffered from various drawbacks for large-scale preparation. Years ago, a general method for the preparation of furoxan from corresponding hydroximidoyl chloride (R–CCl=NOH) with silver carbonate (Ag₂CO₃) was developed in our group. Now this method is extended to prepare 1 from 2. The synthesis involves the treatment of 2 with Ag₂CO₃ in THF at room temperature, with a 3–4 h reaction time, with a yield of 80–90%. Using this method, a one pound batch of the material has been prepared at the lab-scale, but the preparation should be easily scaled to the multikilogram synthesis. This is an environmentally benign process since the preparation generates little hazardous wastes due to the possible recycling of the solvent, THF, and the byproduct, silver chloride.

Authors:

^[1]; DeHope, Alan J. ^[1]; Pagoria, Philip. F. ^[1]

Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)

Publication Date:: 2019-09-13

Research Org.:: Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)

Sponsoring Org.:: USDOE National Nuclear Security Administration (NNSA)

OSTI Identifier:: 1566013

Report Number(s):: LLNL-JRNL-773016
Journal ID: ISSN 1083-6160; 964660

Grant/Contract Number:: AC52-07NA27344

Resource Type:: Accepted Manuscript

Journal Name:: Organic Process Research & Development

Additional Journal Information:: Journal Volume: 23; Journal Issue: 11; Journal ID: ISSN 1083-6160

Publisher:: ACS Publications

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Zhang, Mao-Xi, DeHope, Alan J., and Pagoria, Philip. F. Environmentally Benign and Scalable Preparation of Diethyl Furoxan-3,4-dicarboxylate Using Silver Carbonate as a Nitrile Oxide Generator.  United States: N. p., 2019. 
Web.  doi:10.1021/acs.oprd.9b00228.

Copy to clipboard


                    Zhang, Mao-Xi, DeHope, Alan J., & Pagoria, Philip. F. Environmentally Benign and Scalable Preparation of Diethyl Furoxan-3,4-dicarboxylate Using Silver Carbonate as a Nitrile Oxide Generator.  United States.  https://doi.org/10.1021/acs.oprd.9b00228

Copy to clipboard


                    Zhang, Mao-Xi, DeHope, Alan J., and Pagoria, Philip. F. Fri .  
"Environmentally Benign and Scalable Preparation of Diethyl Furoxan-3,4-dicarboxylate Using Silver Carbonate as a Nitrile Oxide Generator".  United States.  https://doi.org/10.1021/acs.oprd.9b00228.  https://www.osti.gov/servlets/purl/1566013.

Copy to clipboard


                    
@article{osti_1566013,

  title        = {Environmentally Benign and Scalable Preparation of Diethyl Furoxan-3,4-dicarboxylate Using Silver Carbonate as a Nitrile Oxide Generator},

  author       = {Zhang, Mao-Xi and DeHope, Alan J. and Pagoria, Philip. F.},

  abstractNote = {Diethyl furoxan-3,4-dicarboxylate (1) is a starting material for many heterocyclic compounds containing furoxan and furazan rings. Usually, furoxan 1 was prepared via a dimerization of corresponding nitrile oxide generated either by treatment of ethyl 2-chloro-2-(hydroxyimino)-acetate (2) with triethylamine or by nitration or conversion of α-activated ethyl acetate with acetyl nitrate in acetic acid or other catalytic reagents. Both methods are suitable for small-scale but suffered from various drawbacks for large-scale preparation. Years ago, a general method for the preparation of furoxan from corresponding hydroximidoyl chloride (R–CCl=NOH) with silver carbonate (Ag2CO3) was developed in our group. Now this method is extended to prepare 1 from 2. The synthesis involves the treatment of 2 with Ag2CO3 in THF at room temperature, with a 3–4 h reaction time, with a yield of 80–90%. Using this method, a one pound batch of the material has been prepared at the lab-scale, but the preparation should be easily scaled to the multikilogram synthesis. This is an environmentally benign process since the preparation generates little hazardous wastes due to the possible recycling of the solvent, THF, and the byproduct, silver chloride.},

  doi          = {10.1021/acs.oprd.9b00228},

  journal      = {Organic Process Research & Development},

  number       = 11,

  volume       = 23,

  place        = {United States},

  year         = {2019},

  month        = {9}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1021/acs.oprd.9b00228

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 3 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

The Furoxan System as a Useful Tool for Balancing "Hybrids" with Mixed .alpha.1-Antagonist and NO-like Vasodilator Activities
journal, December 1995

Fruttero, Roberta; Boschi, Donatella; Di Stilo, Antonella
Journal of Medicinal Chemistry, Vol. 38, Issue 25
DOI: 10.1021/jm00025a012

π-Facial Selectivity in the Cycloaddition of Nitrile Oxides to 5,6-Dideoxy-5-Enofuranoses
journal, April 1994

Blake, Alexander; Kirkpatrick, Graeme; McGhie, Karen
Journal of Carbohydrate Chemistry, Vol. 13, Issue 3
DOI: 10.1080/07328309408009202

Regio- and Facial-Selective Effects of Allylic Heteroatoms in 1,3-Dipolar Cycloaddition of a Nitrile Oxide
journal, November 1990

Inouye, Yoshinobu; Mitsuya, Morihiro; Tokuhisa, Kenji
Bulletin of the Chemical Society of Japan, Vol. 63, Issue 11
DOI: 10.1246/bcsj.63.3300

Reaction of 3,4-disubstituted 1,2,5-oxadiazole 2-oxides with dipolarophiles
journal, January 1985

Shimizu, Tomio; Hayashi, Yoshiyuki; Taniguchi, Takehiro
Tetrahedron, Vol. 41, Issue 4
DOI: 10.1016/S0040-4020(01)96450-6

Reaction of 3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide with olefins
journal, September 1983

Shimizu, Tomio; Hayashi, Yoshiyuki; Teramura, Kazuhiro
The Journal of Organic Chemistry, Vol. 48, Issue 18
DOI: 10.1021/jo00166a024

Reaction of benzohydroximinoyl chlorides and β-(trifluoromethyl)-acetylenic esters: Synthesis of regioisomeric (trifluoromethyl)-isoxazolecarboxylate esters and oxime addition products
journal, July 2003

Hamper, Bruce C.; Leschinsky, Kindrick L.
Journal of Heterocyclic Chemistry, Vol. 40, Issue 4
DOI: 10.1002/jhet.5570400404

1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues
journal, July 2003

Conti, Dario; Rodriquez, Manuela; Sega, Alessandro
Tetrahedron Letters, Vol. 44, Issue 28
DOI: 10.1016/S0040-4039(03)01195-X

Nitrile oxide cycloadditions to olefinated sugars
journal, January 2003

Colinas, Pedro A.; Jäger, Volker; Lieberknecht, Albrecht
Tetrahedron Letters, Vol. 44, Issue 5
DOI: 10.1016/S0040-4039(02)02665-5

Stereoselective cycloaddition of nitrile oxides to a dispiroketal-protected but-3-ene-1,2-diol
journal, November 1995

Gravestock, Michael B.; Paton, R. Michael; Todd, Christine J.
Tetrahedron: Asymmetry, Vol. 6, Issue 11
DOI: 10.1016/0957-4166(95)00362-S

Base- and Copper-Catalysed Condensation of Primary Activated Nitro Compounds with Enolisable Compounds
journal, December 2009

Trogu, Elena; Cecchi, Luca; De Sarlo, Francesco
European Journal of Organic Chemistry, Vol. 2009, Issue 34
DOI: 10.1002/ejoc.200900802

Reaction of N2O4 with Substituted Dinitromethane Salts as a New Method for the Generation of Nitrile Oxides
journal, January 1992

Makhova, Nina N.; Ovchinnikov, Igor V.; Dubonos, Vladimir G.
Mendeleev Communications, Vol. 2, Issue 3
DOI: 10.1070/MC1992v002n03ABEH000148

Reactions of hexanitroethane with alcohols
journal, December 1983

Tzeng, Dongjaw; Baum, Kurt
The Journal of Organic Chemistry, Vol. 48, Issue 26
DOI: 10.1021/jo00174a053

Nitration of acetoacetate esters by acetyl nitrate. High yield synthesis of nitroacetoacetate and nitroacetate esters
journal, November 1975

Sifniades, Stylianos
The Journal of Organic Chemistry, Vol. 40, Issue 24
DOI: 10.1021/jo00912a020

The Nitrosation of Primary Aliphatic Diazocarbonyl Compounds: Formation of ?-carbonyl nitrile oxides. Preliminary communication
journal, January 1973

Dahn, Hans; Favre, B.; Leresche, J. -P.
Helvetica Chimica Acta, Vol. 56, Issue 1
DOI: 10.1002/hlca.19730560136

Syntheses and Reactions of 2-Substituted Thiazolidines
journal, January 1972

Hirai, Koichi; Matsuda, Hidebumi; Kishida, Yukichi
Chemical and Pharmaceutical Bulletin, Vol. 20, Issue 1
DOI: 10.1248/cpb.20.97

Reaction of Aliphatic Diazo Compounds with Dinitrogen Trioxide. A Facile route to 3,4-Disubstituted 1,2,5-Oxadiazole-2-oxides(Furoxans)
journal, January 1971

Engbersen, J. F. J.; Engberts, J. B. F. N.
Synthetic Communications, Vol. 1, Issue 2
DOI: 10.1080/00397917108081628

Potassium iodate ($$\hbox {KIO}_{3}$$) as a novel reagent for the synthesis of isoxazolines: evaluation of antimicrobial activity of the products
journal, May 2019

Kotian, Sumana Y.; Abishad, P. M.; Byrappa, K.
Journal of Chemical Sciences, Vol. 131, Issue 6
DOI: 10.1007/s12039-019-1622-9

In Situ Generation of Nitrile Oxides from NaCl–Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition
journal, December 2018

Zhao, Guodong; Liang, Lixin; Wen, Chi Ho Ethan
Organic Letters, Vol. 21, Issue 1
DOI: 10.1021/acs.orglett.8b03829

Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles
journal, February 2016

Kesornpun, Chatchai; Aree, Thammarat; Mahidol, Chulabhorn
Angewandte Chemie International Edition, Vol. 55, Issue 12
DOI: 10.1002/anie.201511730

Synthesis of 3-Aryl/benzyl-4,5,6,6a-tetrahydro-3a H -pyrrolo[3,4- d ]isoxazole Derivatives: A Comparison between Conventional, Microwave-Assisted and Flow-Based Methodologies
journal, November 2010

Castellano, Sabrina; Tamborini, Lucia; Viviano, Monica
The Journal of Organic Chemistry, Vol. 75, Issue 21
DOI: 10.1021/jo1014323

Synthesis of α-Nitro Carbonyls via Nitrations in Flow
journal, September 2016

Chentsova, Anna; Ushakov, Dmitry B.; Seeberger, Peter H.
The Journal of Organic Chemistry, Vol. 81, Issue 19
DOI: 10.1021/acs.joc.6b01634

Metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrile oxides
journal, January 2018

Roscales, Silvia; Plumet, Joaquín
Organic & Biomolecular Chemistry, Vol. 16, Issue 44
DOI: 10.1039/C8OB02072H

Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials
journal, June 2017

Pagoria, Philip F.; Zhang, Mao-Xi; Zuckerman, Nathaniel B.
Chemistry of Heterocyclic Compounds, Vol. 53, Issue 6-7
DOI: 10.1007/s10593-017-2122-9

3,6-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazene (BNDD): A Powerful Sensitive Explosive
journal, August 2011

Leonard, Philip; Pollard, Colin; Chavez, David
Synlett, Vol. 2011, Issue 14
DOI: 10.1055/s-0030-1261169

Nitration of α-Oximino Esters and Acids ¹
journal, May 1959

Ungnade, H. E.; Kissinger, L. W.
The Journal of Organic Chemistry, Vol. 24, Issue 5
DOI: 10.1021/jo01087a026

Similar Records in DOE PAGES and OSTI.GOV collections:

Synthesis and characterization of gallium and indium thiolate complexes. Crystal and molecular structures of [M(SC{sub 5}H{sub 4}N){sub 3}] (M = Ga, In), [In(SC{sub 5}H{sub 3}N-3-SiMe{sub 3}){sub 3}], and [M{sub 2}(OC{sub 2}H{sub 4}){sub 2}(SC{sub 5}H{sub 4}N){sub 4}] (M = Ga, In)

Journal Article Rose, D J ; Chang, Yuan Da ; Chen, Qin ; ... - Inorganic Chemistry

The synthesis and characterizations of the monomeric group III thiolate complexes [In(SC{sub 5}H{sub 4}N){sub 3}](1), [In(SC{sub 5}H{sub 3}N-3-SiMe{sub 3}){sub 3}](2), and [Ga(SC{sub 5}H{sub 4}N){sub 3}] (5) and of the binuclear alkoxy-bridged derivatives [M{sub 2}(OC{sub 2}H{sub 5}){sub 2}(SC{sub 5}H{sub 4}N){sub 4}] (M=In (3), Ga (6)) are described. Compounds 1 and 2 are formed in the reaction of the appropriate nitrate salt M(NO{sub 3}){sub 3}{center_dot}xH{sub 2}O with the pyridine-2-thiol derivative in ethanol or water in the presence of triethylamine. In contrast, when the reaction is carried out under strictly anaerobic conditions, using the appropriate metal chloride MCl{sub 3} in ethanol solution, themore »« less
https://doi.org/10.1021/ic00119a019
Investigating 3,4-bis(3-nitrofurazan-4-yl)furoxan detonation with a rapidly tuned density functional tight binding model

Journal Article Lindsey, Rebecca K. ; Bastea, Sorin ; Goldman, Nir ; ... - Journal of Chemical Physics

In this work, we describe a machine learning approach to rapidly tune density functional tight binding models for the description of detonation chemistry in organic molecular materials. Resulting models enable simulations on the several 10s of ps scales characteristic to these processes, with “quantum-accuracy.” We use this approach to investigate early shock chemistry in 3,4-bis(3-nitrofurazan-4-yl)furoxan, a hydrogen-free energetic material known to form onion-like nanocarbon particulates following detonation. We find that the ensuing chemistry is significantly characterized by the formation of large C_xN_yO_z species, which are likely precursors to the experimentally observed carbon condensates. Beyond utility as a means of investigatingmore »« less
https://doi.org/10.1063/5.0047800

Full Text Available
Potentiometric titration of gold, platinum, and some other precious metals

Conference Selig, W S

Gold, platinum, and several other platinum metals can be determined by titration with cetylpyridinium chloride (CPC). CPC forms a precipitate with AuCl{sub 4}{sup {minus}} and PtCl{sub 6}{sup 2{minus}}. Differentiation of AuCl{sub 4{minus}} and PtCl{sub 6}{sup 2{minus}} with this titrant is not possible; however, their sum can be determined. Titration with tetraphenylarsonium chloride at pH 1 is selective for tetrachloroaurate, which thus can be determined in the presence of hexachloroplatinate. Hexachloroosmate(IV), tetrachloroplatinite(II), tetrachloropalladate(II), hexachloropalladate(IV), and hexachloroiridate(IV) can also be determined potentiometrically vs. CPC. The indicating electrode is prepared by coating a spectroscopic graphite rod with a solution of poly(vinyl chloride) (PVC)more »« less
Bis(1,2,4-oxadiazolyl) Furoxan: A Promising Melt-Castable Eutectic Material of Low Sensitivity

Journal Article Johnson, Eric C. ; Bukowski, Eric J. ; Sabatini, Jesse J. ; ... - ChemPlusChem

A scalable synthesis of bis(1,2,4-oxadiazoyl) furoxan, C₆H₂N₆O₄, its physical properties, and its theoretical performance values are described herein. Previous attempts to synthesize this compound required expensive reagents, and/or time-consuming synthesis processes and low overall yields. In addition to disclosing a streamlined synthesis of bis(1,2,4-oxadiazolyl) furoxan, we report its molecular configuration and crystal structure, as well as its correct melting point. Bis(1,2,4-oxadiazolyl) furoxan exhibits a very insensitive behavior to impact, friction, and electrostatic discharge, with a calculated detonation pressure 20 % higher than that of TNT. Given its physical properties and theoretical performance values, this material can be classified as amore »« less
https://doi.org/10.1002/cplu.201800563

Full Text Available
Nuclear medicine program: Progress report for quarter ending June 30, 1988

Technical Report Knapp, Jr, F F ; Ambrose, A P ; Callahan, A P ; ...

This report describes our initial studies on developing techniques of attaching radioisotopes of copper (Cu-64 and Cu-67) and rhenium (Re-186 and Re-188) to proteins. Our work has focussed on the synthesis of para-carboxyalkylphenylglyoxal-bis-(N/sub 4/-methylthiosemi-carbazone) ligands (TSC). Because of the strong binding of Cu(II) to the bis-TSC ligand, the development of bifunctional chelates for attachment of radioisotopes of copper to antibodies is of interest. We have developed an improved synthesis of the requisite ..cap alpha..-ketoaldehyde and 1,2-diketone substrates used for derivatization to the bis-TSC ligand chelates. This approach uses the ''Kornbloom'' method which provides a simple alternative to the usual methodmore »« less

Similar Records

Title: Environmentally Benign and Scalable Preparation of Diethyl Furoxan-3,4-dicarboxylate Using Silver Carbonate as a Nitrile Oxide Generator

Abstract

Citation Formats

The Furoxan System as a Useful Tool for Balancing "Hybrids" with Mixed .alpha.1-Antagonist and NO-like Vasodilator Activities journal, December 1995

π-Facial Selectivity in the Cycloaddition of Nitrile Oxides to 5,6-Dideoxy-5-Enofuranoses journal, April 1994

Regio- and Facial-Selective Effects of Allylic Heteroatoms in 1,3-Dipolar Cycloaddition of a Nitrile Oxide journal, November 1990

Reaction of 3,4-disubstituted 1,2,5-oxadiazole 2-oxides with dipolarophiles journal, January 1985

Reaction of 3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide with olefins journal, September 1983

Reaction of benzohydroximinoyl chlorides and β-(trifluoromethyl)-acetylenic esters: Synthesis of regioisomeric (trifluoromethyl)-isoxazolecarboxylate esters and oxime addition products journal, July 2003

1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues journal, July 2003

Nitrile oxide cycloadditions to olefinated sugars journal, January 2003

Stereoselective cycloaddition of nitrile oxides to a dispiroketal-protected but-3-ene-1,2-diol journal, November 1995

Base- and Copper-Catalysed Condensation of Primary Activated Nitro Compounds with Enolisable Compounds journal, December 2009

Reaction of N2O4 with Substituted Dinitromethane Salts as a New Method for the Generation of Nitrile Oxides journal, January 1992

Reactions of hexanitroethane with alcohols journal, December 1983

Nitration of acetoacetate esters by acetyl nitrate. High yield synthesis of nitroacetoacetate and nitroacetate esters journal, November 1975

The Nitrosation of Primary Aliphatic Diazocarbonyl Compounds: Formation of ?-carbonyl nitrile oxides. Preliminary communication journal, January 1973

Syntheses and Reactions of 2-Substituted Thiazolidines journal, January 1972

Reaction of Aliphatic Diazo Compounds with Dinitrogen Trioxide. A Facile route to 3,4-Disubstituted 1,2,5-Oxadiazole-2-oxides(Furoxans) journal, January 1971

Potassium iodate ($$\hbox {KIO}_{3}$$) as a novel reagent for the synthesis of isoxazolines: evaluation of antimicrobial activity of the products journal, May 2019

In Situ Generation of Nitrile Oxides from NaCl–Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition journal, December 2018

Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles journal, February 2016

Synthesis of 3-Aryl/benzyl-4,5,6,6a-tetrahydro-3a H -pyrrolo[3,4- d ]isoxazole Derivatives: A Comparison between Conventional, Microwave-Assisted and Flow-Based Methodologies journal, November 2010

Synthesis of α-Nitro Carbonyls via Nitrations in Flow journal, September 2016

Metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrile oxides journal, January 2018

Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials journal, June 2017

3,6-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazene (BNDD): A Powerful Sensitive Explosive journal, August 2011

Nitration of α-Oximino Esters and Acids 1 journal, May 1959

The Furoxan System as a Useful Tool for Balancing "Hybrids" with Mixed .alpha.1-Antagonist and NO-like Vasodilator Activities
journal, December 1995

π-Facial Selectivity in the Cycloaddition of Nitrile Oxides to 5,6-Dideoxy-5-Enofuranoses
journal, April 1994

Regio- and Facial-Selective Effects of Allylic Heteroatoms in 1,3-Dipolar Cycloaddition of a Nitrile Oxide
journal, November 1990

Reaction of 3,4-disubstituted 1,2,5-oxadiazole 2-oxides with dipolarophiles
journal, January 1985

Reaction of 3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide with olefins
journal, September 1983

Reaction of benzohydroximinoyl chlorides and β-(trifluoromethyl)-acetylenic esters: Synthesis of regioisomeric (trifluoromethyl)-isoxazolecarboxylate esters and oxime addition products
journal, July 2003

1,3-Cycloaddition of nitrile oxides in ionic liquids. An easier route to 3-carboxy isoxazolines, potential constrained glutamic acid analogues
journal, July 2003

Nitrile oxide cycloadditions to olefinated sugars
journal, January 2003

Stereoselective cycloaddition of nitrile oxides to a dispiroketal-protected but-3-ene-1,2-diol
journal, November 1995

Base- and Copper-Catalysed Condensation of Primary Activated Nitro Compounds with Enolisable Compounds
journal, December 2009

Reaction of N2O4 with Substituted Dinitromethane Salts as a New Method for the Generation of Nitrile Oxides
journal, January 1992

Reactions of hexanitroethane with alcohols
journal, December 1983

Nitration of acetoacetate esters by acetyl nitrate. High yield synthesis of nitroacetoacetate and nitroacetate esters
journal, November 1975

The Nitrosation of Primary Aliphatic Diazocarbonyl Compounds: Formation of ?-carbonyl nitrile oxides. Preliminary communication
journal, January 1973

Syntheses and Reactions of 2-Substituted Thiazolidines
journal, January 1972

Reaction of Aliphatic Diazo Compounds with Dinitrogen Trioxide. A Facile route to 3,4-Disubstituted 1,2,5-Oxadiazole-2-oxides(Furoxans)
journal, January 1971

Potassium iodate ($$\hbox {KIO}_{3}$$) as a novel reagent for the synthesis of isoxazolines: evaluation of antimicrobial activity of the products
journal, May 2019

In Situ Generation of Nitrile Oxides from NaCl–Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition
journal, December 2018

Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles
journal, February 2016

Synthesis of 3-Aryl/benzyl-4,5,6,6a-tetrahydro-3a H -pyrrolo[3,4- d ]isoxazole Derivatives: A Comparison between Conventional, Microwave-Assisted and Flow-Based Methodologies
journal, November 2010

Synthesis of α-Nitro Carbonyls via Nitrations in Flow
journal, September 2016

Metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrile oxides
journal, January 2018

Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials
journal, June 2017

3,6-Bis(4-nitro-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazene (BNDD): A Powerful Sensitive Explosive
journal, August 2011

Nitration of α-Oximino Esters and Acids ¹
journal, May 1959