SYNTHESIS OF 4(5)-ACYL-5(4)-ALKYLIMIDAZOLES FROM SYMMETRICAL 1,3-DIONES

被引：11

作者：

KREBS, EP

BONDI, E

机构：

[1] Pharmazeutische Forschungsabteilung der F. Hoffmann-La Roche & Co. AG, Basel

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 02期

关键词：

D O I：

10.1002/hlca.19790620216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of 4(5)‐Acyl‐5(4)‐alkylimidazoles from Symmetrical 1,3‐Diones A new synthesis of 4(5)‐acyl‐5(4)‐alkylimidazoles 1 is described. The symmetrical 1,3‐diones 5a and 5b were reacted with N2O4 to give the nitro compounds 7a and 7b, respectively; 5c was treated with NaNO2 to give the nitroso compound 7c (Scheme 2). Hydrogenation of 7a, 7b and 7c over Pd/C in acetic acid/acetic formic anhydride yielded the formamides 9a, 9b and 9c, whose cyclization in formamide/formic acid afforded the 4(5)‐acyl‐5(4)‐alkylimidazoles 1a, 1b and 1c, respectively. Oxazoles 11a and 11b were obtained from the corresponding formamides 9a and 9b with methanesulfonic acid/P2O5. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：497 / 506

页数：10

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