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

Cannatelli, Mark D.; Ragauskas, Arthur J.

doi:10.1016/j.tetlet.2016.07.016

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

Journal Article · Wed Jul 06 00:00:00 EDT 2016 · Tetrahedron Letters

DOI:https://doi.org/10.1016/j.tetlet.2016.07.016· OSTI ID:1327722

Cannatelli, Mark D. ^[1]; Ragauskas, Arthur J. ^[2]

Georgia Inst. of Technology, Atlanta, GA (United States)
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)

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.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Joint Institute for Biological Sciences (JIBS)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1327722

Journal Information:: Tetrahedron Letters, Vol. 57, Issue 33; ISSN 0040-4039

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 9 works

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