Proton- and halogen-induced cyclizations of 2-(3-butenyl)quinazolin-4(3H)-ones in the synthesis of pyrrolo[2,1-b]- and pyrrolo[1,2-а]quinazolinone derivatives,Journal of Heterocyclic Chemistry

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Proton- and halogen-induced cyclizations of 2-(3-butenyl)quinazolin-4(3H)-ones in the synthesis of pyrrolo[2,1-b]- and pyrrolo[1,2-а]quinazolinone derivatives
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2022-11-06 , DOI: 10.1002/jhet.4598
Ruslan I. Vaskevych ₁ , Nataliia O. Savinchuk ₁ , Alla I. Vaskevych ₁ , Eduard B. Rusanov ₁ , Denys V. Bylina ₂ , Andrii A. Kyrylchuk ₁ , Mykhailo V. Vovk ₁

Affiliation

With the aim of finding efficient initiators for electrophilic cyclizations of 2-(3-butenyl)quinazolin-4(3H)-ones, their reactions with a number of acids (НCl, CF3COOH, H2SO4, polyphosphoric acid, CF3SO2OH) and halogenating agents (I2, Br2, NIS, NBS) have been studied. As established, CF3SO2OH can be successfully applied in the synthesis of linear 1-methyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-ones while the use of I2, NIS, or NBS readily leads to angular 1-(halomethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones.

中文翻译：

质子和卤素诱导的 2-(3-丁烯基)quinazolin-4(3H)-ones 在吡咯并 [2,1-b]- 和吡咯并 [1,2-а] 喹唑啉酮衍生物合成中的环化

为了寻找 2-(3-butenyl)quinazolin-4(3H)-ones 亲电环化的有效引发剂，它们与许多酸（НCl、CF3COOH、H2SO4、多磷酸、CF3SO2OH）和卤化剂的反应（ I2、Br2、NIS、NBS) 已被研究。正如所确定的那样，CF3SO2OH 可以成功地应用于线性 1-methyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-ones 的合成，而使用 I2、NIS 或 NBS 很容易导致角 1-(halomethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones。

更新日期：2022-11-06

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