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

Yong Gao | Zendy; Changfeng Hu | Zendy; Chengping Wen | Zendy; JiePing Wan | Zendy

Open Access

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

Author(s) -

Yong Gao,

Changfeng Hu,

Chengping Wen,

JiePing Wan

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b01422

Subject(s) - transamination , disulfide bond , catalysis , chemistry , sulfoxide , tandem , combinatorial chemistry , dimethyl disulfide , organic chemistry , sulfur , materials science , biochemistry , composite material , enzyme

The reactions of β-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(sp 2 )-H bond thiolation.

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