Nucleophilic Substitution of Oxazino-/Oxazolino-/Benzoxazin [3,2-b]indazoles: An Effective Route to 1H-Indazolones

被引：21

作者：

Donald, Michael B. ^{[2
]}

Conrad, Wayne E. ^{[2
]}

Oakdale, James S. ^{[2
]}

Butler, Jeffrey D. ^{[2
]}

Haddadin, Makhluf J. ^{[1
]}

Kurth, Mark J. ^{[2
]}

机构：

[1] Amer Univ Beirut, Dept Chem, Beirut, Lebanon

[2] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 11期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

INDAZOLONES; MILD;

D O I：

10.1021/ol100751n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of nucleophiles, thiolates, alkoxides, amines, iodide, and cyanide, react with oxazino-, oxazolino-, and benzoxazin[3,2-b]indazoles under microwave conditions to yield a diverse set of 2-substituted 1H-indazolones. The synthetic utility of these indazoles is further demonstrated by ANRORC (addition of the nucleophile, ring-opening, and ring closure) reactions to yield isomeric pyrazoloindazolones by a process wherein iodide acts first as a nucleophile and subsequently as a leaving group.

引用

页码：2524 / 2527

页数：4

共 20 条

[11] Highly selective isomerization of N-allylamides and N-allylamines [J].