One-Pot Synthesis of 3,4-Dihydropyrimidino[2,1-a]isoindol-6(2H)-one

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Abstract

One-pot synthesis of 3,4-dihydropyrimidino[2,1-a]isoindol-6(2H)-one, an analog of the promising anti-cancer drug batracilin, has been developed. Both acylation of 1,3-diaminopropane with phthalic anhydride and followed by cyclocondensation took place while heating in toluene or ortho-xylene. The highest yield 76% of the target isoindolone was obtained by adding 1,3-diaminopropane to phthalic anhydride in toluene, while reverse order of mixing the reagents, decreases the yield to 60%. The reaction proceeds stepwise, through the formation of 2-(3-aminopropyl)carbamoyl)benzoic acid, which is converted to isoindolone upon heating with 68% yield.

About the authors

G. S Martyanov

Postovsky Institute of Organic Synthesis UB RAS

ORCID iD: 0000-0002-5850-8443
Ekaterinburg, Russia

M. A Barabanov

Postovsky Institute of Organic Synthesis UB RAS

Email: filmsey@mail.ru
ORCID iD: 0009-0000-1152-0317
Ekaterinburg, Russia

A. V Pestov

Postovsky Institute of Organic Synthesis UB RAS

ORCID iD: 0000-0002-4270-3041
Ekaterinburg, Russia

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