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Tunable Synthesis of Disulfide-Functionalized Enaminones and 1,4-Thiazines via the Reactions of Enaminones and ?-Aminoethanethiol.

ABSTRACT: The reactions of ?-aminoethanethiol with N,N-dimethyl enaminones are performed to selectively provide disulfide-functionalized enaminones and 1,4-thiazines. By performing the reaction in water and catalyst-free conditions, the transamination and oxidative S-S coupling between the two substrates take place to give disulfide-functionalized enaminones. On the other hand, by using identical starting materials, the employment of the CuI catalyst in dimethyl sulfoxide enables the selective generation of 1,4-thiazines via tandem transamination and C(sp²)-H bond thiolation.

SUBMITTER: Gao Y

PROVIDER: S-EPMC6645214 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Tunable Synthesis of Disulfide-Functionalized Enaminones and 1,4-Thiazines via the Reactions of Enaminones and β-Aminoethanethiol.

Gao Yong Y Hu Changfeng C Wen Chengping C Wan Jie-Ping JP

ACS omega 20171110 11

The reactions of β-aminoethanethiol with <i>N</i>,<i>N</i>-dimethyl enaminones are performed to selectively provide disulfide-functionalized enaminones and 1,4-thiazines. By performing the reaction in water and catalyst-free conditions, the transamination and oxidative S-S coupling between the two substrates take place to give disulfide-functionalized enaminones. On the other hand, by using identical starting materials, the employment of the CuI catalyst in dimethyl sulfoxide enables the selecti ...[more]

PMID: 31457336

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