NONSTEROIDAL ANTIINFLAMMATORY AGENTS .6. SYNTHESIS OF 10-OXO-5H-PYRROLO[1,2-B]ISOQUINOLINE-3-ACETIC ACID, A CONFORMATIONALLY RESTRICTED ANALOG OF TOLMETIN

被引：10

作者：

CORELLI, F ^{[1
]}

GAROFALO, A ^{[1
]}

MASSA, S ^{[1
]}

SILVESTRI, R ^{[1
]}

PROSINI, P ^{[1
]}

ARTICO, M ^{[1
]}

机构：

[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO FARMACEUT,I-00185 ROME,ITALY

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1990年 / 27卷 / 05期

关键词：

D O I：

10.1002/jhet.5570270557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 10‐oxo‐5H‐pyrrolo[1,2‐b]isoquinoline‐3‐acetic acid 4, a tricyclic analogue of tolmetin which might show significant analgesic‐antiinflammatory activity, has been accomplished in four steps. Alkylation of ethyl 2‐pyrrolylglyoxylate (15) with 2‐cyanobenzyl bromide afforded derivative 16, which was transformed by the Huang‐Minion reaction into the dicarboxylic acid 6. Cyclization of this key intermediate to 17, followed by alkaline hydrolysis, afforded 10‐oxo‐5H‐pyrrolo[1,2–6]isoquinoline‐3‐acetic acid (4). Various attempted syntheses of 6 are also discussed. Copyright © 1990 Journal of Heterocyclic Chemistry

引用

页码：1489 / 1493

页数：5

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