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Facile and one pot synthetic routes for various novel, differently fused and promising heteropolycycles
Author(s) -
Gupta Shallu,
Gupta Poonam,
Sachar Anand,
Sharma R. L.
Publication year - 2010
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.342
Subject(s) - chemistry , thiourea , knoevenagel condensation , ammonium acetate , bifunctional , ethyl cyanoacetate , barbituric acid , malononitrile , methylene , urea , organic chemistry , methanol , medicinal chemistry , combinatorial chemistry , catalysis , high performance liquid chromatography
Four‐component one pot cyclocondensation of aromatic aldehydes 1, ethyl cyanoacetate 2, barbituric acid 3 and ammonium acetate in methanol gave substituted and functionalised pyrido[2,3‐d]pyrimidine derivatives 4 and 4′ after initial Knoevenagel, subsequent Micheal and final heterocyclization reactions . Compounds 4 on reaction with different active methylene compounds resulted in the formation of again functionalized and diversly substituted pyrimidonaphthyridines 5‐7, 9 and benzo[b] pyrimidonaphthyridines 8. The various compounds of systems 7 and 8 on further condensation with the reactive and mostly the bifunctional moieties like urea/thiourea, and 2‐aminopyridine generated the novel and differently fused dipyrimidonaphthyridines 10/11 and pyrimidonaphthyridinoquinazolines 13/14, and pyridopyrimido‐ pyrimido[1,8]naphthyridines 15 and pyrimidonaphthyridino‐ pyridoquinazolines 16, respectively, hitherto unknown in literature. Compounds 7 on condensation with o ‐phenylenediamine produced novel pyrimidonaphthyridinobenzodiazepines 12. Other novel systems like pyrido[2,3‐d;6,5‐d′]dipyrimidines 17, dipyrimido[4,5‐b:5′,4′‐g][1,8]naphthyridines 18, 1,3,4,6,7,8,9,11‐octazabenzo[de]naphthacenes 19, dipyrimido[4,5‐b:5′,4′‐g][1,8]naphthyridines 20, pyrimido[5′,4′:6,7][1,8]naphthyridino[4,3‐b][1,5]benzodiazepines 21, dipyrimido[4,5‐b:4′,5′‐f][1,8]naphthyridines 22 and dipyrimido [4,5‐b:5′,4′‐g][1,8] naphthyridines 23 have also been generated in this study. J. Heterocyclic Chem., (2010).