A regioselective and convenient one-pot multicomponent synthesis of polyfunctionalized 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrido[2,3-d]pyrimidines
- 20 June 2019
- journal article
- research article
- Published by Taylor & Francis Ltd in Synthetic Communications
- Vol. 49 (18), 2401-2410
- https://doi.org/10.1080/00397911.2019.1626892
Abstract
A novel series of 5,7-diamino-4-aryl-6-cyano-2-cyanoimino-3,4-dihydro-1H-pyrido[2,3-d]pyrimidines (aryl-CIDHPPMs) 3a–i was prepared via the one-pot four-component reaction of cyanoguanidine with aromatic aldehydes and malononitrile with molar ratio (1:1:2) using sodium methoxide as catalyst. These new polyfunctionlized aryl-CIDHPPMs were also synthesized by a classical route via reaction of cyanoguanidine with the respective arylidenes of malononitrile dimer under the same condition. In the same manner, the reaction of cyanoguanidine with isatinylidene of malononitrile dimer afforded the new spiro-pyrido[2,3-d]pyrimidines 7. While using aromatic aldehydes having electron donating groups (hydroxyl or dimethylamino groups) gave 4-Amino-2-aryl-6-methoxypyridine-3,5-dicarbonitrile 5a,b.Keywords
This publication has 41 references indexed in Scilit:
- One-pot synthesis of 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidines and their reactionsChemistry of Heterocyclic Compounds, 2012
- Synthesis of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives and their anticancer activityEuropean Journal of Medicinal Chemistry, 2011
- An efficient synthesis of pyrido[2,3-d]pyrimidine derivatives in ionic liquidJournal of Heterocyclic Chemistry, 2010
- An efficient and clean synthesis of pyrido[2,3‐d]pyrimidine‐4,7‐dione derivatives in aqueous mediaJournal of Heterocyclic Chemistry, 2009
- Tautomerism of guanidines studied by 15N NMR: 2-hydrazono-3-phenylquinazolin-4(3H)-ones and related compoundsOrganic & Biomolecular Chemistry, 2009
- New One-Pot Four-Component Synthesis of Disubstituted Pyrido[2,3-d]pyrimidine-6-carboxamide DerivativesJournal of Combinatorial Chemistry, 2009
- Pyridopyrimidine derivatives as inhibitors of cyclic nucleotide synthesis: Application for treatment of diarrheaProceedings of the National Academy of Sciences of the United States of America, 2008
- Synthesis and evaluation of analgesic, anti-inflammatory and ulcerogenic activities of some triazolo- and 2-pyrazolyl-pyrido[2,3-d]-pyrimidinesActa Pharmaceutica, 2008
- Pyrido [2, 3-d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological ActivityArchiv der Pharmazie, 2002
- Antihypertensive activity of 6-arylpyrido[2,3-d]pyrimidin-7-amine derivatives. 2. 7-Acyl amide analogsJournal of Medicinal Chemistry, 1983