A GENERAL METHOD FOR THE SYNTHESIS OF N-UNSUBSTITUTED 3,4-DIARYLPYRROLE-2,5-DICARBOXYLATES

被引：8

作者：

Fukuda, Tsutomu ^{[1
]}

Hayashida, Yukie ^{[1
]}

Iwao, Masatomo ^{[2
]}

机构：

[1] Nagasaki Univ, Grad Sch Sci & Technol, Nagasaki 8528521, Japan

[2] Nagasaki Univ, Dept Appl Chem, Fac Engn, Nagasaki 8528521, Japan

来源：

HETEROCYCLES | 2009年 / 77卷 / 02期

关键词：

N-Unsubstituted 3,4-Diarylpyrrole-2,5-dicarboxylate; Hinsberg Reaction; Suzuki-Miyaura Coupling; 3,4-Diarylpyrrole Marine Alkaloid; G TRIMETHYL ETHER; MARINE NATURAL-PRODUCTS; LAMELLARIN-ALPHA; 20-SULFATE; PERMETHYL STORNIAMIDE-A; EFFICIENT SYNTHESIS; LUKIANOL-A; REGIOSELECTIVE SYNTHESIS; ALKALOID HALITULIN; NINGALIN-B; PYRROLES;

D O I：

10.3987/COM-08-S(F)89

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2,5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diarylpyrrole-2,5-dicarboxylates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.

引用

页码：1105 / 1122

页数：18

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