Reactivity of Hydrazine, Some Hydrazine derivatives and Diamines toward Ethyl 2,2-Dicyano-1-aryl (or alkyl)vinylcarbamate

Fakher Chabchoub,Fethi Zribi,Mansour Salem

doi:10.24297/jac.v10i2.979

Abstract

A series of pyrimidinone and dipyrimidinone derivatives 2a-c, 4a-e and 6a-f has been synthesized via the reaction between ethyl 2,2-dicyano-1-aryl(or alkyl)vinylcarbamate derivatives 1a-d and hydrazine derivatives or diamines. The reactivity of compounds 1a-d toward hydrazine is studied. The result is the formation of triazolones 5a-d rather than pyrimidinone derivatives.

Highlights

Over the years pyrimidinones derivatives have emerged as an interesting class of heterocycles with an astonishingly wide range of applications in pharmaceutical chemistry [1,2,3,4]
We report the synthesis of some new pyrimidinones, dipyrimidinones and triazolones derivatives
Pyrimidine derivatives 2a-c were synthesized by cyclization, involving the reaction of substrates 1a-c with phenylhydrazine in chlorobenzene under reflux

Summary

INTRODUCTION

Over the years pyrimidinones derivatives have emerged as an interesting class of heterocycles with an astonishingly wide range of applications in pharmaceutical chemistry [1,2,3,4]. It is of great interest that functionalized pyrimidinones may possess specific biological properties. Many synthetic procedures exist for the synthesis of pyrimidinones derivatives [11,12,13,14,15]. The development of simple, easy and efficient methodologies to get pyrimidinones is one of the major aspects in organic synthesis. The ethyl 2,2-dicyano-1- aryl (or alkyl)vinylcarbamate derivatives are valuable intermediates in a variety of synthetic transformations. We report the synthesis of some new pyrimidinones, dipyrimidinones and triazolones derivatives

RESULTS AND DISCUSSION

H N N C R2

CONCLUSION