Microwave assisted stereospecific synthesis of (S)-3-substituted 2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido-[3,4-b]indole-1,4-diones

被引：12

作者：

Pandey, SK ^{[1
]}

Awasthi, KK ^{[1
]}

Saxena, AK ^{[1
]}

机构：

[1] Cent Drug Res Inst, Div Med Chem, Lucknow 226001, Uttar Pradesh, India

来源：

TETRAHEDRON | 2001年 / 57卷 / 20期

关键词：

microwave heating; stereospecific; Pictet-Spengler reaction; pyrazino[1 ',2 ': 1.6]pyrido[3,4-b]indole-1,4-dione;

D O I：

10.1016/S0040-4020(01)00334-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new easy way of preparing (S)-3-substituted 2,3,6,7,12,12a-hexahydropyrazino[ 1',2':1,6]pyrido[3,4-b]indole-1,4-diones, an important intermediate compound, is described using microwave irradiation supported on silica gel. The reaction is generalised and good to excellent yields of enantiomerically pure products are obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4437 / 4442

页数：6

共 23 条

[1]

AGARWAL SK, 1990, INDIAN J CHEM B, V29, P80

[2] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[3] Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].

Cui, CB ;

Kakeya, H ;

Osada, H .

TETRAHEDRON, 1997, 53 (01) :59-72

[4] SYNTHESIS OF BETA-CARBOLINE-BENZODIAZEPINE HYBRID MOLECULES AND THEIR AMPUTATED ANALOGS AS NOVEL LIGANDS OF THE BENZODIAZEPINE RECEPTOR [J].

DELLOUVECOURILLON, C ;

DOREY, G ;

POISSONNET, G ;

DOISY, X ;

POTIER, P ;

DODD, RH .

TETRAHEDRON, 1990, 46 (09) :3245-3266

[5]

DUAGAN ACM, 1997, Patent No. 9703985

[6] Synthesis of diverse tetrahydro-β-carboline-3-carboxamides and -2,3-bis-lactams on a versatile 4-hydroxythiophenol-linked solid support [J].

Fantauzzi, PP ;

Yager, KM .

TETRAHEDRON LETTERS, 1998, 39 (11) :1291-1294

[7] STEREOSELECTIVE SYNTHESIS OF VERRUCULOGEN TR-2 FEATURING THE MILD FORMATION OF A DIHYDRO-BETA-CARBOLINE AS AN INTERMEDIATE [J].

HERMKENS, PHH ;

PLATE, R ;

KRUSE, CG ;

SCHEEREN, HW ;

OTTENHEIJM, HCJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3881-3887

[8] Stereochemical issues related to the synthesis of 7,10-dimethyl-7,10,16,16a-tetrahydro-11H-quinazolino[2′,3′:3,4]pyrazino[1,2-b]β-carboline-5,8-diones [J].

Madrigal, A ;

Grande, M ;

Avendaño, C .

TETRAHEDRON-ASYMMETRY, 1998, 9 (17) :3115-3123

[9] Stereocontrolled synthesis of 3,6-dimethyl-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]-β-carboline-1,4-diones [J].

Madrigal, A ;

Grande, M ;

Avendaño, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2724-2727

[10]

PATNAIK G K, 1992, Indian Journal of Experimental Biology, V30, P144

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