Copper-catalyzed intramolecular N-S bond formation by oxidative dehydrogenative cyclization

Zhen Wang; Yoichiro Kuninobu; Motomu Kanai

doi:10.1021/jo401056g

Copper-catalyzed intramolecular N-S bond formation by oxidative dehydrogenative cyclization

Zhen Wang, Yoichiro Kuninobu, Motomu Kanai

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

Abstract

Copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization is described. In this reaction, a new nitrogen-sulfur (N-S) bond is formed by N-H/S-H coupling. The present reaction has high functional group tolerance and gives products in gram scale. This method promotes double cyclization, allowing for synthesis of a drug intermediate.

Original language	English
Pages (from-to)	7337-7342
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	78
Issue number	14
DOIs	https://doi.org/10.1021/jo401056g
Publication status	Published - Jul 19 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo401056g

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abstract = "Copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization is described. In this reaction, a new nitrogen-sulfur (N-S) bond is formed by N-H/S-H coupling. The present reaction has high functional group tolerance and gives products in gram scale. This method promotes double cyclization, allowing for synthesis of a drug intermediate.",

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AU - Wang, Zhen

AU - Kuninobu, Yoichiro

AU - Kanai, Motomu

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Y1 - 2013/7/19

N2 - Copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization is described. In this reaction, a new nitrogen-sulfur (N-S) bond is formed by N-H/S-H coupling. The present reaction has high functional group tolerance and gives products in gram scale. This method promotes double cyclization, allowing for synthesis of a drug intermediate.

AB - Copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization is described. In this reaction, a new nitrogen-sulfur (N-S) bond is formed by N-H/S-H coupling. The present reaction has high functional group tolerance and gives products in gram scale. This method promotes double cyclization, allowing for synthesis of a drug intermediate.

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JO - Journal of Organic Chemistry

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Copper-catalyzed intramolecular N-S bond formation by oxidative dehydrogenative cyclization

Abstract

All Science Journal Classification (ASJC) codes

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