CHEMISTRY OF NITROALKANES .83. HETEROCYCLIC DERIVATIVES OF METHAZONIC ACID . FORMATION OF 5-NITRO-1,2,3,4-TETRAHYDROPYRIMIDINE DERIVATIVES

The derivative produced by the reaction of methaonic acid with p-chloraniline reacts with formaldehyde and primary amines to form 1,3-disubstituted 5-nitro-1,2,3,4-tetrahydropyriimdines. These are readily transaminated at the 1- or 1,3-positions by warming with primary amines. Transamination involves (1) ring opening with loss of a mole of formaldehyde to form a Schiffs base zwitterion, (2) replacement of the amine forming the Schiff.s base, and (3) reclosure of the ring by formaldehyde. © 1969.