Water as an efficient medium for the synthesis of tetrahydro-β-carbolines via Pictet-Spengler reactions

被引：66

作者：

Saha, Biswajit ^{[1
]}

Sharma, Sunil ^{[1
]}

Sawant, Devesh ^{[1
]}

Kundu, Bijoy ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 08期

关键词：

Pictet-Spengler cyclization; beta-carboline; stereoselective reaction; Mannich bases;

D O I：

10.1016/j.tetlet.2006.12.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient protocol for the Pictet-Spengler reaction in water using an acid catalyst has been described. The condensation of tryptophan, tryptamine, and N-b-benzyl tryptophan with different aldehydes having both electron-withdrawing and -donating substituents in the presence of a catalytic amount of TFA in water furnished tetrahydro-beta-carbolines in good isolated yields. A salient feature of the water mediated Pictet-Spengler reaction was the general trend observed during the condensation of Trp-OMe and aryl/aliphatic aldehydes furnishing diastereomeric mixtures with a preference for the cis-isomer. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：1379 / 1383

页数：5

共 28 条

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[24] SYNTHESIS OF NOVEL TETRACYCLIC THIENO[3′,2′:2,3]PYRIDO[4,5-d]PYRIDO[1,2-a]PYRIMIDINONES VIA PICTET-SPENGLER CYCLIZATION
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[J]. HETEROCYCLES, 2017, 94 (07) : 1351 - 1358
[25] Synthesis of highly functionalized β-lactam substituted pyrroloisoquinoline and indolizinoindole system by sequential intermolecular 1,3-dipolar cycloaddition reaction and Pictet-Spengler cyclization
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[J]. Chemistry of Heterocyclic Compounds, 2010, 46 : 711 - 720
[28] PICTET-SPENGLER REACTION IN THE SYNTHESIS OF CONDENSED BENZODIAZEPINES. 2.* SYNTHESIS OF NEW DERIVATIVES OF 11,12-DIHYDROQUINAZOLINE-[3,2-c][2,3]BENZODIAZEPIN-14(6H)-ONES
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[J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (06) : 711 - 720

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