Reactivity of epoxy-ynamides with metal halides: nucleophile (Br/Cl/OH)-assisted tandem intramolecular 5-exo-dig or 6-endo-dig cyclisation and AgF2-promoted oxidation

被引：17

作者：

Anitha, Mandala ^{[1
]}

Shankar, Mallepalli ^{[1
]}

Swamy, K. C. Kumara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 08期

关键词：

ANISOLE-SUBSTITUTED YNAMIDES; GOLD-CATALYZED SYNTHESIS; ALPHA-KETO-IMIDES; CASCADE CYCLIZATION; BOND FORMATION; ACCESS; FUNCTIONALIZATION; DERIVATIVES; OXAZOLONES; INDOLES;

D O I：

10.1039/c9qo00027e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several metal halides react with epoxy-ynamides. Thus, CuBr-mediated concomitant bromination/5-exo-dig cyclisation of epoxy-ynamides affords functionalised 1,3-oxazolidines. In contrast, functionalised 1,4-oxazines are obtained via 6-endo-dig cyclisation of epoxy-ynamides using LiCl or CuF2/H2O. In addition, CuBr is effective for dibromination of functionalised ynamides leading to ,-dibromo-enamides, with the (E) isomer predominating. Formation of epoxy-1,2-dioxo-amides by oxidation of epoxy-ynamides using AgF2 as the oxidising agent is also highlighted.

引用

页码：1133 / 1139

页数：7

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