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Synthesis of new fulvenes containing heterocyclic substituents
Author(s) -
Knight David B.,
Hall Randall W.,
Cleary Darryl G.
Publication year - 1981
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.5570180835
Subject(s) - chemistry , fulvene , tetrahydropyran , cyclopentadiene , fulvenes , methyl iodide , salt (chemistry) , organic chemistry , condensation , iodide , chloromethane , piperidine , medicinal chemistry , ring (chemistry) , catalysis , physics , thermodynamics
Four new fulvene derivatives bearing heterocyclic substituents have been prepared. Base‐promoted condensation of cyclopentadiene with tetrahydropyran‐4‐one, tetrahydrothiopyran‐4‐one, and 1‐methyl‐4‐piperidone afforded 4‐(cyclopentadienylidene)tetrahydropyran 1 , 4‐(cyclopentadienylidene)tetrahydrothiopyran 2 , and N ‐methyl‐4‐(cyclopentadienylidene)piperidine 3 in yields ranging from 28% to 75%. Methylation of 3 with methyl iodide gave the corresponding ammonium salt, 4 .