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

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

Cannatelli, Mark D., and Ragauskas, Arthur J.. Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study. United States: N. p., 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. doi:10.1016/j.tetlet.2016.07.016.
Cannatelli, Mark D., and Ragauskas, Arthur J.. 2016. "Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase – A comparative study". United States. doi: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}
}