Enediynes from aza-enediynes: C,N-dialkynyl imines undergo both aza-Bergman rearrangement and conversion to enediynes and fumaronitriles

被引：20

作者：

Feng, LP

Zhang, AB

Kerwin, SM ^{[1
]}

机构：

[1] Univ Texas, Div Med Chem, Coll Pharm, Austin, TX 78712 USA

[2] Univ Texas, Inst Mol & Cellular Biol, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 10期

关键词：

D O I：

10.1021/ol0600638

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Aza-enediynes (C,N-dialkynyl imines) undergo thermal aza-Bergman rearrangement to beta-alkynyl acrylonitriles through 2,5-didehydropyridine (2,5-ddp) intermediates. Certain aza-enediynes also undergo an alternative process affording enediynes and fumaronitriles. Studies employing a specifically C-13-labeled aza-enediyne show that the conversion to enediyne is second order in aza-enediyne, proceeds by a "head-to-tail" coupling, and affords the (Z)-enediyne.

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页码：1983 / 1986

页数：4

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