Reactions of 2 H ‐3,1‐benzoxazine‐2,4‐(1 H )dione (isatoic anhydride)   with anions of 1,4‐dihydro‐5 H ‐pyrazol‐5‐ones: Synthesis of pyrazolo[5,1‐ b ]quinazolin‐9‐ones | Zendy

Sircar Jagadish C. | Zendy; Capiris Thomas | Zendy; Kesten Stephen J. | Zendy

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Reactions of 2 H ‐3,1‐benzoxazine‐2,4‐(1 H )dione (isatoic anhydride) with anions of 1,4‐dihydro‐5 H ‐pyrazol‐5‐ones: Synthesis of pyrazolo[5,1‐ b ]quinazolin‐9‐ones

Author(s) -

Sircar Jagadish C.,

Capiris Thomas,

Kesten Stephen J.

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.5570180124

Subject(s) - chemistry , nucleophile , medicinal chemistry , organic chemistry , acetic anhydride , ion , catalysis

Reactions of 2 H ‐3,1‐benzoxazine‐2,4‐(1 H )dione (isatoic anhydride) (1) with anions of 1,4‐dihydro‐5 H ‐pyrazol‐5‐ones (2) gave pyrazolo[5,1‐6]quinazolin‐9‐ones (3) via the nucleophilic attack of the anion 2b rather than 2a. However, in the case of 5‐methoxyisatoic anhydride ( 10c) , both products 3e and 11c were obtained. A new synthetic method of preparation of 5‐(alkylthio)‐2‐aminobenzoic acids (18) was described. These acids (18) were used to synthesize a series of substituted pyrazolo[5,1‐ b ]quinazolin‐9‐ones (3) .

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