Synthesis of spiro(indoline-2,3′-hydropyridazine) via an “on-water” [4 + 2] annulation reaction,Organic Chemistry Frontiers

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Synthesis of spiro(indoline-2,3′-hydropyridazine) via an “on-water” [4 + 2] annulation reaction
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-12-22 , DOI: 10.1039/d0qo01422b
Wei-Fang Zuo _{1,

2,

3,

4,

5} , Jin Zhou _{1,

2,

3,

4,

5} , Yu-Ling Wu _{1,

2,

3,

4,

5} , Hua-Ying Fang _{1,

2,

3,

4,

5} , Xing-Jiang Lang _{1,

2,

3,

4,

5} , Ya Li _{1,

2,

3,

4,

5} , Gu Zhan _{1,

2,

3,

4,

5} , Bo Han _{1,

2,

3,

4,

5}

Affiliation

An on-water [4 + 2] annulation reaction between the 2-methyl-3H-indolium salt and α-bromo N-acyl hydrazone has been developed. The environmentally friendly strategy provides the first facile access to spiro(indoline-2,3′-hydropyridazine) scaffolds. Compared with the reaction in organic solvents, the use of water as the sole solvent remarkably improves the reaction efficiency as well as chemoselectivity. This green protocol features high yield, broad substrate scope, and mild reaction conditions.

中文翻译：

通过“水上” [4 + 2]环合反应合成螺（吲哚啉-2,3'-氢哒嗪）

已经开发了2-甲基-3 H-吲哚盐和α-溴N-酰基之间的水上[4 + 2]环化反应。环保策略是第一个便捷地使用螺（吲哚啉-2,3'-氢哒嗪）支架的途径。与在有机溶剂中的反应相比，使用水作为唯一的溶剂显着提高了反应效率以及化学选择性。该绿色方案具有高收率，广泛的底物范围和温和的反应条件。

更新日期：2021-01-07

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