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Paper | Regular issue | Vol 92, No. 9, 2016, pp.1614-1628
Published online, 15th July, 2016
DOI: 10.3987/COM-16-13503
Facile Synthesis of Sulfonyl Amidines by 1,3-Dipolar Cycloaddition between 1-Morpholinocycloalkenes and Sulfonyl Azides without Catalyst

Chiaa Adiche, Mohammed Hamadouche, and Douniazad El Abed*

*Chemistry Department, Faculty of Exact and Applied Sciences, University of Oran 1, Ahmed BenBella, BP 1524 El M’naouar, Oran 31000, Algeria

Abstract

Three new series of sulfonyl amidines were prepared by 1,3-dipolar cycloaddition reaction between 1-morpholinocycloalkenes and various substituted sulfonyl azides without catalyst at room temperature. This reaction yielded unstable bicyclic Δ2-1,2,3-triazoline intermediates which rearranged themselves in situ into amidines by elimination of a nitrogen molecule. The reactions were performed under mild conditions and with moderate to good yields.