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An Expedient Synthesis of a New Calix Frame by Lewis Acid Catalyzed Cyclocondensations of Ketones with Different Heterocyclic Ring Systems
Author(s) -
Nayak Anupam,
Banerji Julie
Publication year - 2014
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.1780
Subject(s) - chemistry , furan , catalysis , lewis acids and bases , ring (chemistry) , pyrrole , column chromatography , organic chemistry , lewis acid catalysis , tin , chloride , combinatorial chemistry , filtration (mathematics) , statistics , mathematics
A facile and highly efficient protocol has been developed for the synthesis of calix[4]pyrroles and tetraoxaquaterenes, in moderate to high yields by reaction of dialkyl or cycloalkyl ketones with pyrrole and furan catalyzed by tin (IV) chloride. Particularly, in the case of furan, instead of tedious column chromatography, simple filtration techniques were employed for purification of the compounds thereby yielding better results and leading to multigram scale synthesis. We also report the first synthesis of the novel tetracyclopentyl tetraoxaquaterene.