Selective electrophilic di- and monofluorinations for the synthesis of 4-difluoromethyl and 4-fluoromethyl quinazolin(thi)ones by a Selectfluor-triggered multi-component reaction,Organic Chemistry Frontiers

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Selective electrophilic di- and monofluorinations for the synthesis of 4-difluoromethyl and 4-fluoromethyl quinazolin(thi)ones by a Selectfluor-triggered multi-component reaction
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-01-20 , DOI: 10.1039/d1qo01728d
Ruiqin Zhang _{1,

2} , Renchao Ma ₁ , Qinjiao Fu ₁ , Rener Chen ₁ , Zhiming Wang ₁ , Lei Wang ₁ , Yongmin Ma _{1,

2}

Affiliation

A simple and efficient domino protocol for the selective synthesis of 4-difluoromethyl and 4-fluoromethyl quinazolin(thi)ones was established from readily available 2-aminoacetophenones and iso(thio)cyanates mediated by Selectfluor. The reaction outcomes are restricted by the reaction environment. Without the use of a base, gem-difluoro-oxylated quinazolin(thi)ones were afforded effectively as a sole product. In contrast, only monofluoro-oxylated analogues were obtained under basic conditions.

中文翻译：

选择性亲电二氟化和单氟化，用于通过 Selectfluor 触发的多组分反应合成 4-二氟甲基和 4-氟甲基喹唑啉（噻）酮

一种简单有效的多米诺骨牌协议，用于选择性合成 4-二氟甲基和 4-氟甲基喹唑啉（噻）酮，由 Selectfluor 介导的现成的 2-氨基苯乙酮和异（硫）氰酸酯建立。反应结果受到反应环境的限制。在不使用碱的情况下，可以有效地提供偕二氟氧化喹唑啉(噻)酮作为唯一产品。相反，在碱性条件下仅获得单氟氧化类似物。

更新日期：2022-01-20

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