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An efficient one‐pot synthesis of 6‐aryl‐5‐cyano‐2‐thiopyrimidinone derivatives and their piperidinium ionic forms, x‐ray crystal structures
Author(s) -
Balalaie Saeed,
Bararjanian Morteza,
Rominger Frank
Publication year - 2006
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.5570430402
Subject(s) - chemistry , thiourea , piperidine , aryl , benzaldehyde , ionic bonding , alkyl , condensation , ionic compound , crystal structure , ionic liquid , organic chemistry , polymer chemistry , medicinal chemistry , catalysis , ion , physics , thermodynamics
Three‐component condensation of benzaldehyde derivatives, alkyl cyanoacetates and thiourea in the presence of piperidine in reflux condition provides a direct route to piperidinium 6‐aryl‐5‐cyano 2‐thiopyrimidonate salts in good yields. These reactions were also carried out under microwave irradiation. The yields of products under the microwave condition were better as compared to the reflux media. The acidification of these ionic forms resulted in the formation of 6‐aryl‐5‐cyano‐2‐thiopyrimidone derivatives. The X‐ray structures of the ionic forms ( 4, 5 , and 7 ) show that there are anionic thiopyrimidinone skeletons hydrogen bridged with piperidinium cations.