Synthesis of pyrido[2,3‐d]pyrimidines in the reaction of 6‐amino‐2,3‐dihydro‐2‐thioxo‐4(1H)‐pyrimidinone with chalcones

Abstract

6‐Amino‐2,3‐dihydro‐2‐thioxo‐4(1H)‐pyrimidinone (1) reacts in boiling DMF with α,/β‐unsaturated ketones 2 yielding the pyrido[2,3‐d]pyrimidine systems 5 and 6, respectively. The orientation in the addition process can be determined by nmr measurements, especially by NOE difference spectroscopy. The products do not correspond to a normal Skraup or Doebner‐v. Miller synthesis. Copyright © 1992 Journal of Heterocyclic Chemistry