Efficient Synthesis of (Z)-4-((Substituted phenylamino)methylidene)isoquinoline-1,3(2H,4H)-diones Using the Eschenmoser Coupling Reaction,Synthesis

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Efficient Synthesis of (Z)-4-((Substituted phenylamino)methylidene)isoquinoline-1,3(2H,4H)-diones Using the Eschenmoser Coupling Reaction
Synthesis ( IF 2.2 ) Pub Date : 2023-11-29 , DOI: 10.1055/a-2198-1589
Lukas Marek ₁ , Jiri Vana ₁ , Jan Svoboda ₁ , Marketa Svobodova ₁ , Jiri Hanusek _{2,

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Affiliation

A novel synthetic strategy involving the Eschenmoser coupling reaction of 4-bromoisoquinoline-1,3(2H,4H)-diones with substituted thioformanilides, thioacetanilides, and thiobenzanilides gave 18 (Z)-4-((substituted phenylamino)methylidene)isoquinoline-1,3(2H,4H)-diones. The reaction occurs under mild conditions (DMF or MeCN, 25–60 °C) without any base or thiophile and in good yields (43–95%). Furthermore, for the synthesis of starting thioformanilides carrying basic substituents, a new thioacylation protocol was developed that involves a thioacylating agent formed from carbon disulfide and lithium triethylborohydride.

中文翻译：

利用 Eschenmoser 偶联反应高效合成 (Z)-4-((取代苯氨基)亚甲基)异喹啉-1,3(2H,4H)-二酮

一种新颖的合成策略，涉及 4-溴异喹啉-1,3(2 H ,4 H )-二酮与取代的硫代甲苯胺、硫代乙酰苯胺和硫代苯甲酰苯胺的 Eschenmoser 偶联反应，得到 18 ( Z )-4-((取代的苯氨基)亚甲基)异喹啉-1,3(2 H ,4 H )-二酮。该反应在温和条件下（DMF 或 MeCN，25–60 °C）发生，无需任何碱或亲硫剂，且收率良好（43–95%）。此外，为了合成带有碱性取代基的起始硫代甲酰苯胺，开发了一种新的硫代酰化方案，其中涉及由二硫化碳和三乙基硼氢化锂形成的硫代酰化剂。

更新日期：2023-11-30

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