Directed metalation of pyridinesulphonamides. Synthesis of pyridine‐fused isothiazoles and 1,2‐oxathioles | Zendy

Alo Babajide I. | Zendy; Familoni Oluwole B. | Zendy; Marsais Francis | Zendy; Queguiner Guy | Zendy

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Directed metalation of pyridinesulphonamides. Synthesis of pyridine‐fused isothiazoles and 1,2‐oxathioles

Author(s) -

Alo Babajide I.,

Familoni Oluwole B.,

Marsais Francis,

Queguiner Guy

Publication year - 1992

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.5570290109

Subject(s) - benzophenone , chemistry , metalation , lithium diisopropylamide , pyridine , lithium (medication) , medicinal chemistry , organic chemistry , ion , medicine , deprotonation , endocrinology

4‐Lithio‐ N‐t ‐butylpyridine‐3‐sulphonamide reacted with benzophenone and carbon dioxide respectively to give the corresponding intermediates which on appropriate treatment gave isothiazolo[5,4‐ c ]pyridin‐3‐one 1,1‐dioxides. Metalation of 2‐ and 4‐( N,N ‐dialkylaminosulphonyl)pyridines with lithium diisopropylamide (LDA) gave anions which reacted with benzophenone to give carbinols which thermally cyclised to 1,2‐oxathiolo[3,4‐b]pyridine and 1,2‐oxathiolo[4,3‐ c ]pyridine respectively.

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