(L)-Proline-catalysed novel tandem reactions of 1-substituted piperidin-4-ones with (E)-4-arylbut-3-en-2-ones:: N-substituent mediated product selectivity and synthesis of novel nitrogen heterocycles

被引：33

作者：

Srinivasan, Murugesan ^{[1
]}

Perumal, Subbu ^{[1
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India

来源：

TETRAHEDRON | 2007年 / 63卷 / 13期

关键词：

(L)-proline; 1-substituted piperidin-4-ones; (E)-4-arylbut-3-en2-ones; isoquinolines; azabicyclo[3.3.1]nonan-9-ones; tandem Robinson annulation; Michael addition; Aldol reaction;

D O I：

10.1016/j.tet.2007.01.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(L)-Proline-catalysed reaction of 1-alkyl/aralkylpiperidin-4-ones with (E)-4-arylbut-3-en-2-ones furnishes novel isoquinoline derivatives, with two or three rings, in good yields via tandem Robinson annulation-Michael addition(s) sequences, while the reaction of 1-arylpiperidin-4-ones with (E)-4-arylbut-3-en-2-ones affords 3-azabicyclo[3.3.1]nonan-9-ones via a tandem Michael addition-aldol reaction sequence. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2865 / 2874

页数：10

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