In(OTf)3-catalyzed tandem aza-Piancatelli rearrangement/Michael reaction for the synthesis of 3,4-dihydro-2H-benzo[b][1,4]thiazine and oxazine derivatives

被引：33

作者：

Reddy, B. V. Subba ^{[1
]}

Reddy, Y. Vikram

Lakshumma, P. Subba

Narasimhulu, G.

Yadav, J. S.

Sridhar, B. ^{[1
]}

Reddy, P. Purushotham ^{[2
]}

Kunwar, A. C. ^{[2
]}

机构：

[1] Indian Inst Chem Technol, Ctr Nucl Magnet Resonance, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

来源：

RSC ADVANCES | 2012年 / 2卷 / 28期

关键词：

1,4-BENZOXAZINE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION; VERSATILE; CATALYST; 3-COMPONENT; MECHANISM; ANALOGS; POTENT; AGENTS;

D O I：

10.1039/c2ra21591h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Furan-2-yl(phenyl) methanol derivatives undergo smooth aza-Piancatelli rearrangement with 2-aminothiophenol and 2-aminophenol in the presence of 10 mol% In(OTf)(3) in acetonitrile at room temperature to afford the corresponding 3,4-dihydro-2H-benzo[b][1,4]thiazine or oxazine derivatives respectively in good yields with high selectivity in short reaction times. The salient features of this methodology are good yields, high selectivity, low catalyst loading and faster reaction times. The structure of the products was established by nOe studies and X-ray crystallography.

引用

页码：10661 / 10666

页数：6

共 38 条

[1] Synthesis of new fused and spiro heterocyclic systems from 3,5-pyrazolidinediones [J].