Synthesis of N-(tosylmethyl) carbodiimides and their application in the synthesis of 2-amino-1, 3-oxazoles from aldehydes

AM Van Leusen, HJ Jeuring, J Wildeman…

Index: Leusen, Albert M. van; Jeuring, Hans J.; Wildeman, Jurjen; Nispen, Simon P. J. M. van Journal of Organic Chemistry, 1981 , vol. 46, # 10 p. 2069 - 2072

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Citation Number: 13

Abstract

A series of N-(tosylmethy1) carbodiimides (TosCH2N= C= NR1, 3) have been prepared from the corresponding thioureas. Carbodiimides 3 with R'= triphenylmethyl or tert-butyl are useful synthons in a new one-step synthesis of 2-(alkylamino)-1, 3-oxazoles 10 from aromatic aldehydes. Acid-induced removal of the triphenylmethyl group from 10 gives 2- amino-1, 3-oxazoles (11).