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Wang J, Li J, Zhu Q. Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles. Org Lett. 2015;17(21):5336-9doi: 10.1021/acs.orglett.5b02694.
Wang, J., Li, J., & Zhu, Q. (2015). Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles. Organic letters, 17(21), 5336-9. https://doi.org/10.1021/acs.orglett.5b02694
Wang, Jian, et al. "Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles." Organic letters vol. 17,21 (2015): 5336-9. doi: https://doi.org/10.1021/acs.orglett.5b02694
Wang J, Li J, Zhu Q. Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles. Org Lett. 2015 Nov 06;17(21):5336-9. doi: 10.1021/acs.orglett.5b02694. Epub 2015 Oct 28. PMID: 26509678.
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Org Lett. 2015 Nov 06;17(21):5336-9. doi: 10.1021/acs.orglett.5b02694. Epub 2015 Oct 28.

Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[d]imidazothiazoles.

Organic letters

Jian Wang, Jing Li, Qiang Zhu

Affiliations

  1. State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , 190 Kaiyuan Avenue, Guangzhou 510530, China.

PMID: 26509678 DOI: 10.1021/acs.orglett.5b02694

Abstract

A tunable route to both isomers of benzo[d]imidazothiazole has been developed through copper-promoted cycloaddition of α-methylenyl isocyanides with benzothiazoles. When the C2 position of benzothiazole is linked to a C-H or C-C bond, benzo[d]imidazo[2,1-b]thiazoles are obtained through a novel rearrangement via C-S bond cleavage and formation of a new C-S bond. When 2-chloro- or 2-bromobenzothiazoles are used under the same reaction conditions, the isomeric benzo[d]imidazo[5,1-b]thiazoles are formed selectively. These reactions proceed smoothly in moderate to excellent yields at room temperature, and a wide range of functional groups are tolerated.

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