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Abstract <p>A one-pot synthesis of 3,4-dihydropyrimidino[2,1-<i>a</i>]isoindol-6(2<i>H</i>)-one, an analog of the promising anticancer drug batracylin, involving the acylation of 1,3-diaminopropane with phthalic anhydride followed by cyclocondensation under heating in toluene or <i>o</i>-xylene, was developed. The highest yield of the target isoindolone of 76% was obtained by adding 1,3-diaminopropane to phthalic anhydride in toluene, while when the order of reagent addition was reversed, the yield decreased to 60%. The reaction occurred stepwise through the formation of 2-[(3-aminopropyl)carbamoyl)]benzoic acid and its subsequent conversion to isoindolone under heating in a yield of 68%.</p>

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

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • G. S. Martyanov,
  • M. A. Barabanov,
  • A. V. Pestov

摘要

Abstract

A one-pot synthesis of 3,4-dihydropyrimidino[2,1-a]isoindol-6(2H)-one, an analog of the promising anticancer drug batracylin, involving the acylation of 1,3-diaminopropane with phthalic anhydride followed by cyclocondensation under heating in toluene or o-xylene, was developed. The highest yield of the target isoindolone of 76% was obtained by adding 1,3-diaminopropane to phthalic anhydride in toluene, while when the order of reagent addition was reversed, the yield decreased to 60%. The reaction occurred stepwise through the formation of 2-[(3-aminopropyl)carbamoyl)]benzoic acid and its subsequent conversion to isoindolone under heating in a yield of 68%.