NOTEWORTHY MECHANISTIC PRECEDENCE IN THE EXCLUSIVE FORMATION OF ONE REGIOISOMER IN THE BECKMANN REARRANGEMENT OF KETOXIMES OF 4-PIPERIDONES ANNULATED TO PYRAZOLO-INDOLE NUCLEUS BY ORGANOCATALYST DERIVED FROM TCT AND DMF

被引：12

作者：

Tyagi, Ruchi ^{[1
]}

Kaur, Navjeet ^{[1
]}

Singh, Bhawani ^{[1
]}

Kishore, D. ^{[1
]}

机构：

[1] Banasthali Univ, Dept Chem, Banasthali 304022, India

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 01期

关键词：

Beckmann rearrangement; Fischer indolization; Japp-Kilingemann reaction; oxoazacarbazoles; oxocarbazoles; pyrazole; TCT-DMF complex; EFFICIENT;

D O I：

10.1080/00397911.2011.589558

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Application of a very mild protocol to the Beckmann rearrangement of ketoximes of pyrazolo annulated oxocarbazole 5a and oxoazacarbazole 5b with the organocatalyst derived from 2,4,6-trichloro[1,3,5] triazine (TCT) and dimethylformamide (DMF) has been explored to provide a regioselective formation of the corresponding azepine 6a and 1,4-diazepine 6b respectively in good yield and purity. The mechanistic precedence for the exclusive formation of only one regioisomer has been discussed.

引用

页码：16 / 25

页数：10