Rhenium-Catalyzed Regioselective Synthesis of Multisubstituted Pyridines from β-Enamino Ketones and Alkynes via C-C Bond Cleavage

被引：80

作者：

Yamamoto, Shun-ichi ^{[1
]}

Okamoto, Kana ^{[1
]}

Murakoso, Makiko ^{[1
]}

Kuninobu, Yoichiro ^{[1
]}

Takai, Kazuhiko ^{[1
]}

机构：

[1] Okayama Univ, Div Chem & Biotechnol, Grad Sch Nat Sci & Technol, Kita Ku, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 12期

关键词：

CARBON SINGLE BOND; ONE-POT SYNTHESIS; ALPHA; BETA-UNSATURATED KETOXIMES; TERMINAL ACETYLENES; H BOND; ISOQUINOLINES; INSERTION; HETEROCYCLES; DERIVATIVES; IMINES;

D O I：

10.1021/ol301273j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl beta-enamino ketones with alkynes in the presence of the rhenium catalyst, Re-2(CO)(10), gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon carbon single bond of beta-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.

引用

页码：3182 / 3185

页数：4

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