Ecofriendly syntheses of phenothiazones and related structures facilitated by laccase - a comparative study

TETRAHEDRON LETTERS

卷:57

Article

Cannatelli, Mark D.¹  Ragauskas, Arthur J.^1,2,3 

[1] Georgia Inst Technol, Sch Chem & Biochem, Renewable Bioprod Inst, Atlanta, GA 30332 USA

[2] Oak Ridge Natl Lab, Biosci Div, Joint Inst Biol Sci, Oak Ridge, TN 37831 USA

[3] Univ Tennessee, Dept Chem & Biomol Engn, Dept Forestry Wildlife & Fisheries, Knoxville, TN 37996 USA

关键词: Biocatalysis;    Green chemistry;    Laccase;    Phenothiazones;    Thiol-amine;   

DOI  :  10.1016/j.tetlet.2016.07.016

来源: Elsevier

【 摘 要 】

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. This study provides a sustainable approach to the synthesis of a biologically important class of compounds. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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