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Shen GL, Sun J, Yan CG. Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Org Biomol Chem. 2015;13(44):10929-38doi: 10.1039/c5ob01374g.
Shen, G. L., Sun, J., & Yan, C. G. (2015). Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Organic & biomolecular chemistry, 13(44), 10929-38. https://doi.org/10.1039/c5ob01374g
Shen, Guo-Liang, et al. "Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles." Organic & biomolecular chemistry vol. 13,44 (2015): 10929-38. doi: https://doi.org/10.1039/c5ob01374g
Shen GL, Sun J, Yan CG. Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles. Org Biomol Chem. 2015 Nov 28;13(44):10929-38. doi: 10.1039/c5ob01374g. Epub 2015 Sep 16. PMID: 26373777.
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Org Biomol Chem. 2015 Nov 28;13(44):10929-38. doi: 10.1039/c5ob01374g. Epub 2015 Sep 16.

Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles.

Organic & biomolecular chemistry

Guo-Liang Shen, Jing Sun, Chao-Guo Yan

Affiliations

  1. College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China. [email protected].

PMID: 26373777 DOI: 10.1039/c5ob01374g

Abstract

The domino cycloaddition reactions of N-phenacylbenzothiazolium bromides with 3-phenacylideneoxindoles or ethyl 2-(2-oxoindolin-3-ylidene)acetates in ethanol at room temperature in the presence of triethylamine as a base afforded functionalized spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] in good yields and with high diastereoselectivity. The similar reactions of N-phenacylthiazolium bromides with 3-phenacylideneoxindoles resulted in the corresponding functionalized spiro[indoline-3,7'-pyrrolo[2,1-b]thiazoles] in satisfactory yields and also with high diastereoselectivity.

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