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Synthesis of pyrido[2,3‐ d ]pyrimidines in the reaction of 6‐amino‐2,3‐dihydro‐2‐thioxo‐4(1 H )‐pyrimidinone with chalcones
Author(s) -
Quiroga Jairo,
Insuasty Braulio,
Sanchez Adolfo,
Nogueras Manuel,
Meier Herbert
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290502
Subject(s) - chemistry , pyrimidine , boiling , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry
6‐Amino‐2,3‐dihydro‐2‐thioxo‐4(1 H )‐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.