ALKYL 3-BROMO-3-NITROACRYLATES – CONVENIENT BUILDING BLOCKS FOR THE CONSTRUCTION OF BENZO-FUSED SIX-MEMBERED N,N-, N,O- AND FIVE-MEMBERED O,O-HETEROCYCLES

Abstract

The reactions of alkyl 3-bromo-3-nitroacrylates with N,N-, N,O-, and О,О-o-phenylene bisnucleophiles resulted in the formation of benzo-fused heterocycles: reactions with о-phenylenediamines and о-aminophenols gave six-membered N,N- and N,O-heterocycles – (Z)3-nitromethylidene-3,4-dihydroquinoxalin-2(1Н)-ones and (Z)-3-nitromethylidene-3,4dihydro-2Н-1,4-benzoxazin-2-ones, while the use of pyrocatechols led to the formation of a five-membered O,Oheterocyclic system, providing alkyl 2-(nitromethyl)-1,3-benzodioxole-2-carboxylates. The nitroenamine moiety of the obtained six-membered heterocycles was shown to undergo tautomeric transformations.

Authors:

Sergey V. Makarenko, Kirill D. Sadykov, Ruslan I. Baichurin