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Title: Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine: Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine

Authors:
ORCiD logo [1]; ORCiD logo [1]
  1. Department of Chemistry, Tennessee Technological University, 55 University Drive 38505-0001 Cookeville TN USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1604479
Grant/Contract Number:  
[SC0018033]
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
European Journal of Organic Chemistry
Additional Journal Information:
[Journal Name: European Journal of Organic Chemistry Journal Volume: 2020 Journal Issue: 12]; Journal ID: ISSN 1434-193X
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Gulledge, Zachary Z., and Carrick, Jesse D. Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine: Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine. Germany: N. p., 2020. Web. doi:10.1002/ejoc.201901811.
Gulledge, Zachary Z., & Carrick, Jesse D. Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine: Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine. Germany. doi:10.1002/ejoc.201901811.
Gulledge, Zachary Z., and Carrick, Jesse D. Fri . "Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine: Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine". Germany. doi:10.1002/ejoc.201901811.
@article{osti_1604479,
title = {Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine: Deprotection of N - tert -Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition-Elimination with 3-Methoxypropylamine},
author = {Gulledge, Zachary Z. and Carrick, Jesse D.},
abstractNote = {},
doi = {10.1002/ejoc.201901811},
journal = {European Journal of Organic Chemistry},
number = [12],
volume = [2020],
place = {Germany},
year = {2020},
month = {3}
}

Journal Article:
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Works referenced in this record:

Novel Practical Deprotection of N-Boc Compounds Using Fluorinated Alcohols
journal, October 2008

  • Choy, Jason; Jaime-Figueroa, Saul; Jiang, Laurence
  • Synthetic Communications, Vol. 38, Issue 21
  • DOI: 10.1080/00397910802238718

Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view
journal, July 2017


Metal-Free Transamidation of Secondary Amides via Selective N–C Cleavage under Mild Conditions
journal, March 2017


Selective removal of the N-BOC protective group using silica gel at low pressure
journal, February 1996


NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist
journal, May 2010

  • Fulmer, Gregory R.; Miller, Alexander J. M.; Sherden, Nathaniel H.
  • Organometallics, Vol. 29, Issue 9
  • DOI: 10.1021/om100106e

Selective nitrolytic deprotection of N -BOC-amines and N -BOC-amino acids derivatives
journal, October 2001


Complexation and Extraction of Trivalent Actinides and Lanthanides by Triazinylpyridine N -Donor Ligands
journal, October 2012

  • Panak, Petra J.; Geist, Andreas
  • Chemical Reviews, Vol. 113, Issue 2
  • DOI: 10.1021/cr3003399

Templated Chromophore Assembly by Dynamic Covalent Bonds
journal, December 2015

  • Rocard, Lou; Berezin, Andrey; De Leo, Federica
  • Angewandte Chemie, Vol. 127, Issue 52
  • DOI: 10.1002/ange.201507186

Recyclable Hypervalent-Iodine-Mediated Dehydrogenative Cyclopropanation under Metal-Free Conditions
journal, November 2016


Structures of Highly Twisted Amides Relevant to Amide N−C Cross-Coupling: Evidence for Ground-State Amide Destabilization
journal, August 2016

  • Pace, Vittorio; Holzer, Wolfgang; Meng, Guangrong
  • Chemistry - A European Journal, Vol. 22, Issue 41
  • DOI: 10.1002/chem.201603543

N -Acyl-Glutarimides: Privileged Scaffolds in Amide N-C Bond Cross-Coupling: N -Acyl-Glutarimides: Privileged Scaffolds in Amide N-C Bond Cross-Coupling
journal, March 2018

  • Meng, Guangrong; Szostak, Michal
  • European Journal of Organic Chemistry, Vol. 2018, Issue 20-21
  • DOI: 10.1002/ejoc.201800109

Medicinal chemistry of indole derivatives: Current to future therapeutic prospectives
journal, August 2019


Benzofuran and Indole: Promising Scaffolds for Drug Development in Alzheimer's Disease
journal, June 2018


Oxidative C–H/C–H Coupling Reactions between Two (Hetero)arenes
journal, January 2017


Structural absorption by barbule microstructures of super black bird of paradise feathers
journal, January 2018


Mechanochemical Pd(II)-Catalyzed Direct and C-2-Selective Arylation of Indoles
journal, August 2019

  • Das, Dharmendra; Bhutia, Zigmee T.; Chatterjee, Amrita
  • The Journal of Organic Chemistry, Vol. 84, Issue 17
  • DOI: 10.1021/acs.joc.9b01280

Complexation and Separation of Lanthanides(III) and Actinides(III) by Heterocyclic N-Donors in Solutions
journal, October 2008


Metal-Free Transamidation of Secondary Amides by N–C Cleavage
journal, August 2019

  • Rahman, Md. Mahbubur; Li, Guangchen; Szostak, Michal
  • The Journal of Organic Chemistry, Vol. 84, Issue 18
  • DOI: 10.1021/acs.joc.9b02013

Structure–activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template
journal, July 2013

  • Tran, Phuong-Thao; Hoang, Van-Hai; Thorat, Shivaji A.
  • Bioorganic & Medicinal Chemistry, Vol. 21, Issue 13
  • DOI: 10.1016/j.bmc.2013.04.005

Synthetic studies on β-lactam antibiotics. VII. Mild removal of the benzyl ester protecting group with aluminum trichloride
journal, January 1979


Simple and Selective Removal of the t ‐Butyloxycarbonyl (Boc) Protecting Group on Indoles, Pyrroles, Indazoles, and Carbolines
journal, February 2007

  • Ravinder, K.; Reddy, A. Vijender; Mahesh, K. Chinni
  • Synthetic Communications, Vol. 37, Issue 2
  • DOI: 10.1080/00397910601033724

Dual Brønsted Acid/Nucleophilic Activation of Carbonylimidazole Derivatives
journal, April 2012

  • Heller, Stephen T.; Fu, Tingting; Sarpong, Richmond
  • Organic Letters, Vol. 14, Issue 8
  • DOI: 10.1021/ol300339q

Recent progress in the synthesis of phosphorus-containing indole derivatives
journal, January 2018

  • Chen, Long; Zou, Yun-Xiang
  • Organic & Biomolecular Chemistry, Vol. 16, Issue 41
  • DOI: 10.1039/C8OB02100G

A Two-Step Procedure for the Overall Transamidation of 8-Aminoquinoline Amides Proceeding via the Intermediate N -Acyl-Boc-Carbamates
journal, March 2018

  • Verho, Oscar; Pourghasemi Lati, Monireh; Oschmann, Michael
  • The Journal of Organic Chemistry, Vol. 83, Issue 8
  • DOI: 10.1021/acs.joc.8b00174

Reversible Twisting of Primary Amides via Ground State N–C(O) Destabilization: Highly Twisted Rotationally Inverted Acyclic Amides
journal, January 2018

  • Meng, Guangrong; Shi, Shicheng; Lalancette, Roger
  • Journal of the American Chemical Society, Vol. 140, Issue 2
  • DOI: 10.1021/jacs.7b11309

Utilisation du groupement cyanométhyle comme motif protecteur des phénols, amines et carbamates
journal, November 1993


N-methoxy-n-methylamides as effective acylating agents
journal, January 1981


Separation of americium from europium using 3,3′-dimethoxy-phenyl-bis-1,2,4-triazinyl-2,6-pyridine
journal, March 2017


The natural and synthetic indole weaponry against bacteria
journal, August 2018


Pd-Catalyzed Diamination of 1,2,4-Triazinyl Complexant Scaffolds
journal, June 2015

  • Tai, Serene; Dover, Evan J.; Marchi, Sydney V.
  • The Journal of Organic Chemistry, Vol. 80, Issue 12
  • DOI: 10.1021/acs.joc.5b00710

Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters
journal, August 2019


Total Synthesis of Adrenocorticotrophic Hormone
journal, July 1963


Chemoselective Esterification and Amidation of Carboxylic Acids with Imidazole Carbamates and Ureas
journal, October 2010

  • Heller, Stephen T.; Sarpong, Richmond
  • Organic Letters, Vol. 12, Issue 20
  • DOI: 10.1021/ol1018882

Suzuki–Miyaura Cross-Coupling of N -Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N–C Cleavage
journal, June 2017


Regioselective zincation of indazoles using TMP2Zn and Negishi cross-coupling with aryl and heteroaryl iodides
journal, January 2012

  • Unsinn, Andreas; Knochel, Paul
  • Chemical Communications, Vol. 48, Issue 21
  • DOI: 10.1039/c2cc17804d

Transamidation of N -acyl-glutarimides with amines
journal, January 2018

  • Liu, Yongmei; Achtenhagen, Marcel; Liu, Ruzhang
  • Organic & Biomolecular Chemistry, Vol. 16, Issue 8
  • DOI: 10.1039/C7OB02874A

Chemistry of Bridged Lactams: Recent Developments
journal, January 2019


Thermolytic removal of t-butyloxycarbonyl (BOC) protecting group on indoles and pyrroles
journal, January 1985


Organic Material Based Fluorescent Sensor for Hg2+: a Brief Review on Recent Development
journal, September 2016

  • Saleem, Muhammad; Rafiq, Muhammad; Hanif, Muhammad
  • Journal of Fluorescence, Vol. 27, Issue 1
  • DOI: 10.1007/s10895-016-1933-x

Synthesis of Tridentate [1,2,4] Triazinyl-Pyridin-2-yl Indole Lewis Basic Complexants via Pd-Catalyzed Suzuki–Miyaura Cross-Coupling
journal, October 2019


NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities
journal, October 1997

  • Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham
  • The Journal of Organic Chemistry, Vol. 62, Issue 21
  • DOI: 10.1021/jo971176v

Boiling water-catalyzed neutral and selective N-Boc deprotection
journal, January 2009

  • Wang, Jia; Liang, Yan-Liang; Qu, Jin
  • Chemical Communications, Issue 34
  • DOI: 10.1039/b910239f

The use of aluminum chloride for removal of Boc groups on 5′-amino-2′,5′-dideoxyoligonucleotides during solid-phase synthesis
journal, January 1998


Synthesis of a Gln-Phe Hydroxy-ethylene Dipeptide Isostere
journal, December 2004

  • Haug, Bengt Erik; Rich, Daniel H.
  • Organic Letters, Vol. 6, Issue 25
  • DOI: 10.1021/ol047879y

Highly Chemoselective, Transition-Metal-Free Transamidation of Unactivated Amides and Direct Amidation of Alkyl Esters by N–C/O–C Cleavage
journal, June 2019

  • Li, Guangchen; Ji, Chong-Lei; Hong, Xin
  • Journal of the American Chemical Society, Vol. 141, Issue 28
  • DOI: 10.1021/jacs.9b04136

Mushroom-Derived Indole Alkaloids
journal, June 2017


Templated Chromophore Assembly by Dynamic Covalent Bonds
journal, December 2015

  • Rocard, Lou; Berezin, Andrey; De Leo, Federica
  • Angewandte Chemie International Edition, Vol. 54, Issue 52
  • DOI: 10.1002/anie.201507186

Lewis Acid-Mediated Selective Removal of N-tert-Butoxycarbonyl Protective Group (t-Boc)
journal, January 1999


11-Step Total Synthesis of Teleocidins B-1–B-4
journal, December 2018

  • Nakamura, Hugh; Yasui, Kosuke; Kanda, Yuzuru
  • Journal of the American Chemical Society, Vol. 141, Issue 4
  • DOI: 10.1021/jacs.8b13697

Flexible and Convergent Total Synthesis of Cyclotheonamide B
journal, June 1997

  • Bastiaans, Harold M. M.; van der Baan, Juul L.; Ottenheijm, Harry C. J.
  • The Journal of Organic Chemistry, Vol. 62, Issue 12
  • DOI: 10.1021/jo961447m

Indole Alkaloid Synthesis Facilitated by Photoredox Catalytic Radical Cascade Reactions
journal, March 2019