Chemoselective reduction of a lactam carbonyl group in the presence of a gem-dicarboxylate by sodium borohydride and iodine:: a facile entry to N-aryl trisubstituted pyrroles

被引：19

作者：

Haldar, P ^{[1
]}

Ray, JK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 45期

关键词：

chemoselective; lactam; reduction; pyrrole;

D O I：

10.1016/j.tetlet.2003.09.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several N-aryl gamma-lactam gem dicarboxylates were chemoselectively reduced to cyclic amine diesters by using sodium borohydride-iodine system. The reduction in all cases was completed within 2.5 h after refluxing in THF. The cyclic amine products were isolated after aqueous (acidic) workup in good yields. Hydrolytic decarboxylation followed by dehydrogenation produced N-aryl carboethoxy pyrroles. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8229 / 8231

页数：3

共 26 条

[1] ANTIFUNGAL AGENTS .9. 3-ARYL-4-[ALPHA-(1H-IMIDAZOL-1-YL)ARYLMETHYL]PYRROLES - A NEW CLASS OF POTENT ANTICANDIDA AGENTS [J].

ARTICO, M ;

DISANTO, R ;

COSTI, R ;

MASSA, S ;

RETICO, A ;

ARTICO, M ;

APUZZO, G ;

SIMONETTI, G ;

STRIPPOLI, V .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (21) :4223-4233

[2]

BTTERSBY AR, 1995, ANTEW CHEM INT ED EN, V34, P383

[3]

BTTERSBY AR, 1995, ANGEW CHEM, V107, P421

[4] Facile reduction of tertiary lactams to cyclic amines with 9-borabicyclo[3.3.1]nonane (9-BBN) [J].

Collins, CJ ;

Lanz, M ;

Singaram, B .

TETRAHEDRON LETTERS, 1999, 40 (19) :3673-3676

[5] The pyrrole moiety as a template for COX-1/COX-2 inhibitors [J].

Dannhardt, G ;

Kiefer, W ;

Krämer, G ;

Maehrlein, S ;

Nowe, U ;

Fiebich, B .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (05) :499-510

[6] SYNTHESIS OF (2S,3S)-[3-2H1]-PROLINE AND (2S,3R)-[2,3-2H2]-PROLINE [J].

DIETERICH, P ;

YOUNG, DW .

TETRAHEDRON LETTERS, 1993, 34 (34) :5455-5458

[7] Aminoborohydrides.: 11.: Facile reduction of N-alkyl lactams to the corresponding amines using lithium aminoborohydrides [J].

Flaniken, JM ;

Collins, CJ ;

Lanz, M ;

Singaram, B .

ORGANIC LETTERS, 1999, 1 (05) :799-801

[8] SYNTHESIS OF (-)-SWAINSONINE AND (-)-8-EPI-SWAINSONINE FROM (S)-GLUTAMIC AND (R)-GLUTAMIC ACID-DERIVATIVES [J].

IKOTA, N ;

HANAKI, A .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (10) :2712-2718

[9] Studies on gamma-lactams: Synthesis of some 3-aryl-1,3a,4,9b-tetrahydrobenzo[e]indole-2,5-dione derivatives and its implication in the total synthesis of functionalized 17-azasteroids [J].

Kar, GK ;

Ramesh, D ;

Chatterjee, BG ;

Ray, JK .

JOURNAL OF CHEMICAL RESEARCH-S, 1997, (03) :80-81

[10] Synthesis of some thieno gamma lactam monocarboxylic acids with high antibacterial activity: A new look at an old molecular system [J].

Kar, GK ;

Roy, BC ;

Das Adhikari, S ;

Ray, JK ;

Brahma, NK .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (12) :2397-2403

← 1 2 3 →