5,6-dihydro-4H-1,2-oxazines in organic synthesis:: Catalytic hydrogenation of [(5,6-dihydro-4H-1,2-oxazin-3-yl)methyl]malonates to methyl 7-oxo-1-oxa-6-azaspiro[4.4]nonane-8-carboxylates

被引：11

作者：

Sukhorukov, Alexey Yu. ^{[1
]}

Lesiv, Alexey V.

Khomutova, Yulia A. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

Nelyubina, Yulia V. ^{[2
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2008年 / 08期

关键词：

5,6-dihydro-4H-1,2-oxazines; reduction; oxaazaspirononanones; imines;

D O I：

10.1055/s-2008-106003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[(5,6-Dihydro-4H-1,2-oxazin-3-yl)methyl]malonates undergo a cascade transformation into substituted methyl 7-oxo-1-oxa-6-azaspiro[4.4]nonane-8-carboxylates under catalytic hydrogenation conditions over Raney nickel. A mechanistic scheme involving initial N-O bond cleavage with the formation of imines as key intermediates is suggested.

引用

页码：1205 / 1220

页数：16

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