Preparation and alkylation of 1,5‐dihydro‐3 H ‐1,2,4‐thiadiazolo[3,4‐ b ]quinazolin‐5‐one 2,2‐dioxides | Zendy

Demers James P. | Zendy; Sulsky Richard | Zendy; Klaubert Dieter H. | Zendy

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Preparation and alkylation of 1,5‐dihydro‐3 H ‐1,2,4‐thiadiazolo[3,4‐ b ]quinazolin‐5‐one 2,2‐dioxides

Author(s) -

Demers James P.,

Sulsky Richard,

Klaubert Dieter H.

Publication year - 1989

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.5570260606

Subject(s) - chemistry , sodium hydride , alkylation , sodium salt , dimethylformamide , sodium , medicinal chemistry , salt (chemistry) , organic chemistry , inorganic chemistry , catalysis , solvent

1,5‐Dihydro‐3 H ‐1,2,4‐thiadiazolo[3,4‐ b ]quinazolin‐5‐one 2,2‐dioxides ( 3 ) are prepared by reaction of isatoic anhydrides with methyl N ‐(chloromethanesulfonyl)carbamimidothioate ( 6 ). The sodium salt of 3a , generated with sodium hydride in N,N ‐dimethylformamide, is alkylated excusively on N‐10. An improved preparation of 6 is described, utilizing a two‐phase sulfonylation.

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