Entry to nitrogen-containing heterocycles by based-promoted heterocyclization on allenylamides of L-α-aminoacids

被引：28
作者：
Broggini, Gianluigi [1 ]
Galli, Simona [1 ]
Rigamonti, Micol [1 ]
Sottocornola, Silvia [1 ]
Zecchi, Gaetano [1 ]
机构：
[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 13期
关键词：
Allenes; Heterocyclization; Hydroamination; Microwave irradiation; Imidazolidinones; Pyrazinones; Pyrroles; ENDO-MODE CYCLIZATION; 1,3-DIPOLAR CYCLOADDITIONS; PYRROLE DERIVATIVES; ALLENES; BROMOALLENES; CARBOCYCLES; SULFOXIDES; OXACYCLES; ABSENCE;
D O I：
10.1016/j.tetlet.2009.01.074
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Allenylamides of Boc-protected alpha-aminoacids easily gave in basic medium heterocyclic products arising from attack of the NH group on the inside C-C double bond of the 1,2-diene moiety, namely imidazolidinones, pyrazinones, and a pyrrole compound. The microwave-assisted heterocyclization occurred cleanly at C-beta of the allenyl group with formation of pyrazin-2-ones having an endo- or exocyclic double bond. (C) 2009 Elsevier Ltd. All rights reserved.
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页码：1447 / 1449
页数：3
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