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Title: Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study

Abstract

The biocatalytic synthesis of phenothiazones and related compounds has been achieved in an aqueous system under mild conditions facilitated by laccase oxidation. It was found that by coupling 2-aminothiophenol directly with 1,4-quinones, the product yields could be significantly increased compared to generating the 1,4-quinones in situ from the corresponding hydroquinones via laccase oxidation. However, laccase still proved to be pivotal for achieving highest product yields by catalyzing the final oxidation step. Furthermore, a difference in reactivity of aromatic and aliphatic amines toward 1,4-naphthoquinone is observed. Furthermore, this study provides a sustainable approach to the synthesis of a biologically important class of compounds.

Authors:
 [1];  [2]
  1. Georgia Inst. of Technology, Atlanta, GA (United States)
  2. Georgia Inst. of Technology, Atlanta, GA (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of Tennessee, Knoxville, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Joint Institute for Biological Sciences (JIBS)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1327722
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Tetrahedron Letters
Additional Journal Information:
Journal Volume: 57; Journal Issue: 33; Journal ID: ISSN 0040-4039
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; biocatalysis; green chemistry; laccase; phenothiazones; thiol-amine

Citation Formats

Cannatelli, Mark D., and Ragauskas, Arthur J. Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study. United States: N. p., 2016. Web. doi:10.1016/j.tetlet.2016.07.016.
Cannatelli, Mark D., & Ragauskas, Arthur J. Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study. United States. https://doi.org/10.1016/j.tetlet.2016.07.016
Cannatelli, Mark D., and Ragauskas, Arthur J. Wed . "Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study". United States. https://doi.org/10.1016/j.tetlet.2016.07.016. https://www.osti.gov/servlets/purl/1327722.
@article{osti_1327722,
title = {Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study},
author = {Cannatelli, Mark D. and Ragauskas, Arthur J.},
abstractNote = {The biocatalytic synthesis of phenothiazones and related compounds has been achieved in an aqueous system under mild conditions facilitated by laccase oxidation. It was found that by coupling 2-aminothiophenol directly with 1,4-quinones, the product yields could be significantly increased compared to generating the 1,4-quinones in situ from the corresponding hydroquinones via laccase oxidation. However, laccase still proved to be pivotal for achieving highest product yields by catalyzing the final oxidation step. Furthermore, a difference in reactivity of aromatic and aliphatic amines toward 1,4-naphthoquinone is observed. Furthermore, this study provides a sustainable approach to the synthesis of a biologically important class of compounds.},
doi = {10.1016/j.tetlet.2016.07.016},
journal = {Tetrahedron Letters},
number = 33,
volume = 57,
place = {United States},
year = {2016},
month = {7}
}

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