Formation of Condensed 1H-Pyrrol-2-ylphosphonates and 1,2-Dihydropyridin-2-ylphosphonates via Kabachnik-Fields Reaction of Acetylenic Aldehydes and Subsequent 5-exo-dig or 6-endo-dig Cyclizations

被引：24

作者：

Buksnaitiene, Rita ^{[1
]}

Urbanaite, Aurelija ^{[1
]}

Cikotiene, Inga ^{[1
]}

机构：

[1] Vilnius State Univ, Dept Organ Chem, Fac Chem, LT-03225 Vilnius, Lithuania

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 14期

关键词：

ELECTROPHILIC CYCLIZATION; BIOLOGICAL EVALUATION; POTENT INHIBITORS; ANTICANCER AGENTS; IODINE; DERIVATIVES; ANALOGS; ALKYNES; ACIDS; GOLD;

D O I：

10.1021/jo501011u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Kabachnik-Fields reactions of various carbocyclic or heterocyclic acetylenic aldehydes together with subsequent Lewis acid catalyzed cyclizations have been studied. It was found that 5-exo-dig versus 6-endo-dig cyclization mode strongly depends on the structure of starting materials. Thus, nonaromatic acetylenic alpha-anilinomethylphosphonates underwent gold(III)-catalyzed or iodine-mediated 5-exo-dig cyclization to 1H-pyrrol-2-ylphosphonates. In contrast, electron-withdrawing heteroaromatic substrates formed 1,2-dihydropyridin-2-yl-phosphonate ring containing materials via an exclusive 6-endo-dig ring-closure process. The dual mode of cyclization is possible only for alpha-amino (2-alkynylphenyl)methylphosphonates containing a benzene ring.

引用

页码：6532 / 6553

页数：22

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