Acid-catalyzed cyclization reactions. IX. Formation of oxazolinium and thiazolinium cation from N-allyl and substituted N-allylamides,-urethans,-ureas, and-thioureas

SP McManus, JT Carroll…

Index: McManus,S.P. et al. Journal of Organic Chemistry, 1970 , vol. 35, p. 3768 - 3774

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Citation Number: 22

Abstract

N-Allyl and substituted N-allylamides,-urethans,-ureas, and-thioureas have been cyclized in 60-96% sulfuric acid to their corresponding oxazolinium and thiazolinium cations. By drowning certain of these acid solutions into base, a useful synthetic route to 2-oxazolines and 2-thiazolines has been demonstrated. The formation of oxazolinium (2a-0) and thiazolinium (2p-r) cations was studied by nmr techniques. In general, the simple N-allyl ...