Development of a new synthesis of 3-(1H-tetrazol-5-yl)-4(3H)-quinazolinone, sodium saltviaan amidine intermediate

Author:

Vinogradoff Anna P.,Peet Norton P.

Publisher

Wiley

Subject

Organic Chemistry

Reference20 articles.

1. N. P. Peet and S. Sunder, U. S. Patent 4,419,357 (Dec. 6, 1983).

2. 3-(1H-Tetrazol-5-yl)-4(3H)-quinazolinone sodium salt (MDL 427): a new antiallergic agent

3. Ortho Esters, Imidic Esters and Amidines. IV. The Mechanism of the Reaction of Aniline with Ethyl Orthoformate1

4. From refluxing ethyl acetate for 4 days, Dowanol PM (glycol ether products) at 100° for 4 days, refluxing toluene (in a Dean Stark apparatus for removal of solvent) for 24 hours, or from slow heating in diphenyl ether at 190°, the sole material found was unreacted amidine 11. Neither 11 nor 7 were recovered from diphenyl ether upon brief heating at 240°. Heating in N/N-dimethylformamide at 140° for 24 hours gave products of amidine bond cleavage. When fusion was attempted by brief immersion of 11 in an oil bath between 200-210°, spectra showed no 7 or 11 present. Proton nmr of spectra of aliquots concentrated from acidic media (catalytic hydrochloric acid, Dowanol PM, 80° catalytic p-toluene-sulfonic acid, refluxing toluene) showed no 11 or 7.

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1. A one-pot pseudo nine-component isocyanide-based reaction: synthesis of a new class of zinc 1,5-disubstituted 1H-tetrazol-5-yl coordination complexes;Tetrahedron Letters;2011-08

2. References;Chemistry of Heterocyclic Compounds: A Series Of Monographs;2008-01-02

3. Volume 4 References;Comprehensive Heterocyclic Chemistry II;1996

4. Tetrazoles;Comprehensive Heterocyclic Chemistry II;1996

5. Facile Synthesis of Tetrazolylchromonoids and Related Compounds;Archiv der Pharmazie;1994

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