I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines

被引：15

作者：

Asthana, Mrityunjaya ^{[1
]}

Sharma, Neha ^{[1
]}

Kumar, Ritush ^{[1
]}

Singh, Jay Bahadur ^{[1
]}

Singh, Radhey M. ^{[1
]}

机构：

[1] Banaras Hindu Univ, Ctr Adv Study, Dept Chem, Varanasi 221005, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 31期

关键词：

Iodine; Catalyzed; Tetracyclic, furothiopyrano[2,3-b]quinolines; Sulfonium; 3-Homoallylquinoline-2-thiones; MICROWAVE-ASSISTED SYNTHESIS; ONE-POT SYNTHESIS; DERIVATIVES; QUINOLINE; ANNULATION; ALCOHOLS; REAGENT; ROUTE; BONDS;

D O I：

10.1016/j.tetlet.2014.06.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

I-2-catalyzed base-free reactions of 3-homoallylquinoline-2-thiones have been described for the synthesis of tetracyclic quinolines, tetrahydrofuro [2',4':4,6]thiopyrano[2,3-Nquinolines in excellent yields. Similarly, I2-catalyzed reactions could proceed to tricyclic quinolines from hydroxyl group protected 3-homoallylquinoline-2-thiones. However, deprotection of group in tricyclic quinoline with HI again transformed into tetracyclic quinoline. The sulfonium salt intermediate has been proposed to explain these reactions. (C) Elsevier Ltd. All rights reserved.

引用

页码：4378 / 4381

页数：4

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