InBr3-and AgOTf-catalyzed beckmann rearrangement of (E)-benzoheterocyclic oximes

被引：17

作者：

Tandon, Vishnu K. ^{[1
]}

Awasthi, Anoop K. ^{[1
]}

Maurya, Hardesh K. ^{[1
]}

Mishra, Pushyamitra ^{[1
]}

机构：

[1] Univ Lucknow, Dept Chem, Lucknow 226007, Uttar Pradesh, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2012年 / 49卷 / 02期

关键词：

DERIVATIVES; KETOXIMES; ACID; DEHYDRATION; FACILE; AGENTS; MILD;

D O I：

10.1002/jhet.438

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Beckmann rearrangement of (E)-4-chromanone oxime, (E)-5-oximino-3,4-dihydro-1(2H)-benzoxepines, and (E)-5-oximino-3,4-dihydro-1(2H)-benzothiepine are catalyzed by InBr3 and AgOTf in refluxing acetonitrile resulting in the formation of pharmaceutically active heterocycles benzoxazepin-4-one, 5-oxo-benzoxazocines, and 5-oxo-benzothiazocine derivative, respectively, in excellent yield. J. Heterocyclic Chem., (2012).

引用

页码：424 / 427

页数：4

共 9 条

[1] PEG-SO3H as catalyst for the Beckmann rearrangement and dehydration of oximes
Wang, Xi Cun
Li, Lei
Quan, Zheng Jun
Gong, Hai Peng
Ye, He Lin
Cao, Xiao Feng
CHINESE CHEMICAL LETTERS, 2009, 20 (06) : 651 - 655
[2] AgOTf-catalyzed dehydrative [3+2] annulation of aziridines with 2-naphthols
Kaicharla, Trinadh
Jacob, Anu
Gonnade, Rajesh G.
Biju, Akkattu T.
CHEMICAL COMMUNICATIONS, 2017, 53 (58) : 8219 - 8222
[3] Synthesis of Polycyclic 3,3?-Biindoles via AgOTf-Catalyzed Nucleophilic Addition and Cycloisomerization
Zhao, Yulei
Li, Shai
Fan, Yuhang
Wang, Huimin
Kang, Xin
Ji, Zhongyin
Tian, Laijin
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) : 6418 - 6425
[4] Silica-supported dichlorophosphate catalyzed Beckmann rearrangement and dehydration of oximes under microwave irradiation
Li, Zheng
Lu, Zhong
LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (06) : 495 - 501
[5] Ph3P/I2-CATALYZED BECKMANN REARRANGEMENT OF KETOXIMES INTO AMIDES
Xu, Feng
Wang, Ni-Ge
Tian, You-Ping
Chen, Yong-Mei
Liu, Wei-Chun
SYNTHETIC COMMUNICATIONS, 2012, 42 (23) : 3532 - 3539
[6] Beckmann rearrangement of acetophenone oximes to the corresponding amides organo-catalyzed by trifluoroacetic acid for sustainable NSAIDs synthesis
Quartarone, Giuseppe
Rancan, Elia
Ronchin, Lucio
Vavasori, Andrea
APPLIED CATALYSIS A-GENERAL, 2014, 472 : 167 - 177
[7] (PPh3)AuCl/AgOTf-Catalyzed Intermolecular Hydroamination of Alkynes with Sulfonamides To Form N-Sulfonyl Imines
Cui, Dong-Mei
Zheng, Jin-Zhou
Yang, Liu-Yang
Zhang, Chen
SYNLETT, 2010, (05) : 809 - 811
[8] Microwave-Assisted Beckmann Rearrangement of Aryl Ketoximes Catalyzed by In(OTf)3 in Ionic Liquid
Sugamoto, Kazuhiro
Matsushita, Yoh-ichi
Matsui, Takanao
SYNTHETIC COMMUNICATIONS, 2011, 41 (06) : 879 - 884
[9] Selective synthesis of novel pyridopyrimido annulated analogues of azepinones from Beckmann rearrangement of corresponding oximes by the 2,4,6-trichloro-1,3,5-triazine and dimethyl formamide reagent
Arora, Deepika
Arora, Sakshi
Kumar, Sudesh
Kishore, Dharma
Dwivedi, Jaya
JOURNAL OF CHEMICAL SCIENCES, 2021, 133 (04)

← 1 →