Synthesis of new fulvenes containing heterocyclic substituents | Zendy

Knight David B. | Zendy; Hall Randall W. | Zendy; Cleary Darryl G. | Zendy

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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 .

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