Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer-Schuster Rearrangement, Anti-Michael Addition/C(sp3)-H Functionalization, and Azacyclization

被引：22

作者：

Yaragorla, Srinivasarao ^{[1
]}

Dada, Ravikrishna ^{[1
]}

Rajesh, P. ^{[1
]}

Sharma, Manju ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, PO Cent Univ, Hyderabad 500046, Andhra Pradesh, India

来源：

ACS OMEGA | 2018年 / 3卷 / 03期

关键词：

SPIROOXINDOLE NATURAL-PRODUCTS; PROPARGYLIC ALCOHOLS; ORGANOLITHIUM REAGENTS; SELECTIVE SYNTHESIS; CASCADE SYNTHESIS; GOLD; ADDITIONS; CATALYSIS; ALDOL; METAL;

D O I：

10.1021/acsomega.8b00147

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot, sequential Meyer-Schuster (MS) rearrangement of oxindole-derived propargyl alcohols to the corresponding alpha, beta-unsaturated enones and their anti-Michael addition, followed by intramolecular azacyclization is described in a highly regioselective manner using Ca(OTf)(2) as the promoter. Further, we described the one-pot MS rearrangement, followed by C-(sp3)-H functionalization of 2-methyl azaarenes at a-carbon of these doubly activated alkenes. Control experiments and computational calculations were performed to propose the reaction mechanism.

引用

页码：2934 / 2946

页数：13

共 36 条

[1] Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer-Schuster Rearrangement, Anti-Michael Addition/C(sp3)-H Functionalization, and Azacyclization (vol 3, pg 2934, 2018)
Yaragorla, Srinivasarao
Dada, Ravikrishna
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ACS OMEGA, 2018, 3 (04): : 3804 - 3804
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