An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies

被引：14

作者：

Ansari, Arshad J. ^{[1
]}

Wani, Aabid Abdullah ^{[2
]}

Maurya, Antim K. ^{[3
]}

Verma, Sarika ^{[4
]}

Agnihotri, Vijai K. ^{[3
]}

Sharon, Ashoke ^{[4
]}

Bharatam, Prasad, V ^{[2
]}

Sawant, Devesh M. ^{[1
]}

机构：

[1] Cent Univ Rajasthan, Sch Chem Sci & Pharm, NH 8, Ajmer 305817, Raj, India

[2] NIPER, Dept Med Chem, Mohali 160062, Punjab, India

[3] CSIR, IHBT, Nat Prod Chem & Proc Dev Div, Palampur 176061, Himachal Prades, India

[4] Birla Inst Technol, Dept Chem, Ranchi 835215, Jharkhand, India

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 98期

关键词：

H BOND FUNCTIONALIZATION; ONE-POT; IMINES; ACIDS; MILD;

D O I：

10.1039/c9cc06751e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A serendipitous discovery of [1,3]-sulfonyl migration has been made in the two-component reaction of azomethine imine and allenoates. Current methodology involving N-S bond cleavage and C-S bond formation provided easy access to biologically important arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazolines. Subsequently, a one-pot sequential protocol has been developed from the easily available starting material. The mechanistic investigation using quantum chemical methods revealed that the sulfonyl migration step is a concerted [1,3]-sigmatropic shift.

引用

页码：14825 / 14828

页数：4

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