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Issue 16, 2009
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The [3 + 2] cycloaddition reaction of thiazole carbene-derived C-C-Se 1,3-dipoles: a concise and highly efficient strategy for the construction of multifunctional dihydroselenophenes and selenopheno[2,3-b]pyrazines

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Abstract

The first study on the reaction of C+-C-Se 1,3-dipoles with electron-deficient alkenes and alkyne is reported. 2-Arylselenocarbamoylthiazolium inner salts, the unique thiazole carbene-derived C+-C-Se 1,3-dipoles, reacted efficiently with methoxycarbonylallenes or dimethyl acetylenedicarboxylate to produce dihydroselenophenes or selenopheno[2,3-b]pyrazines, respectively, in high yields. Both reactions probably proceeded via a [3 + 2] cycloaddition of C+-C-Se 1,3-dipoles with alkenes or alkyne followed by different transformations of the thiazole-spiro-selenophene intermediates. This work provides a concise and efficient strategy for the construction of multifunctional dihydroselenophenes and selenopheno[2,3-b]pyrazines, which are not easy accessible by other methods.

Graphical abstract: The [3 + 2] cycloaddition reaction of thiazole carbene-derived C-C-Se 1,3-dipoles: a concise and highly efficient strategy for the construction of multifunctional dihydroselenophenes and selenopheno[2,3-b]pyrazines

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Publication details

The article was received on 05 Mar 2009, accepted on 22 May 2009 and first published on 29 Jun 2009


Article type: Paper
DOI: 10.1039/B904575A
Org. Biomol. Chem., 2009,7, 3264-3270

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    The [3 + 2] cycloaddition reaction of thiazole carbene-derived C-C-Se 1,3-dipoles: a concise and highly efficient strategy for the construction of multifunctional dihydroselenophenes and selenopheno[2,3-b]pyrazines

    J. Zhang and Y. Cheng, Org. Biomol. Chem., 2009, 7, 3264
    DOI: 10.1039/B904575A

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