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
收藏
页码：5274 / 5281
页数：8
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