Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines

被引：19

作者：

Haut, Franz-Lucas ^{[1
,2
]}

Feichtinger, Niklas J. ^{[1
,2
]}

Plangger, Immanuel ^{[1
,2
]}

Wein, Lukas A. ^{[1
,2
]}

Mueller, Mira ^{[1
,2
]}

Streit, Tim-Niclas ^{[1
,2
]}

Wurst, Klaus ^{[2
,3
]}

Podewitz, Maren ^{[2
,3
]}

Magauer, Thomas ^{[1
,2
]}

机构：

[1] Leopold Franzens Univ Innsbruck, Inst Organ Chem, A-6020 Innsbruck, Austria

[2] Leopold Franzens Univ Innsbruck, Ctr Mol Biosci, A-6020 Innsbruck, Austria

[3] Leopold Franzens Univ Innsbruck, Inst Gen Inorgan & Theoret Chem, A-6020 Innsbruck, Austria

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 24期

基金：

奥地利科学基金会;

关键词：

PUMMERER; ELECTROCYCLIZATION; CONSTRUCTION;

D O I：

10.1021/jacs.1c04835

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present a modular, synthetic entry to polysubstituted pyrroles employing readily available 2,5-dihydrothiophenes. Ring-opening of the heterocycle provides access to a panel of 1,3-dienes which undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The transformation is conducted in an open flask and proceeds at ambient temperatures (23 degrees C) in nondry solvents. A careful adjustment of the electronics and sterics of the 1,3-diene precursor allows for the isolation of key intermediates. DFT studies identified a reaction mechanism that features a 6 pi-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.

引用

页码：9002 / 9008

页数：7

共 39 条

[1] Pyrrole: An insight into recent pharmacological advances with structure activity relationship [J].