Facile Entry to 3,4-Dihydro-1H-pyrrolo[2,1-c][1,4]oxazines through the oxa-Pictet-Spengler Reaction

被引：1

作者：

Reddy, Chada Raji ^{[1
]}

Burra, Amarender Goud ^{[1
]}

Singarapu, Kiran K. ^{[2
]}

Gree, Rene ^{[3
]}

机构：

[1] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, Ctr NMR & Struct Chem, Hyderabad 500007, Andhra Pradesh, India

[3] CNRS UMR 6226, Inst Sci Chim Rennes, Ave Gen Leclerc, F-35042 Rennes, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 31期

关键词：

Synthetic methods; Cyclization; Fused-ring systems; Nitrogen heterocycles; Alkaloids; BAYLIS-HILLMAN ACETATES; ACETYLENIC ALDEHYDES; ALKALOIDS; ACORTATARINS; PYRROLES; POLLENOPYRROSIDE; CONSTRUCTION; ISOCHROMANS;

D O I：

10.1002/ejoc.201600928

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intermolecular approach to the construction of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines is reported for the first time using the oxa-Pictet-Spengler reaction. The method involves a sequence of carbon-carbon-and carbon-oxygenbond formation between a substituted 2-(1H-pyrrol-1-yl)ethan-1-ol and an aldehyde/ketone. p-Toluenesulfonic acid (pTSA) was identified as a suitable catalyst to promote the reaction. The method provides a one-step conversion of various aldehydes/ketones into the corresponding 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines.

引用

页码：5274 / 5281

页数：8

共 43 条

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CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 1062 - 1066

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