Dibenzo[b,f]pyrazolo[1,5-d][1,4]oxazepines: Facile Construction of a Rare Heterocyclic System via Tandem Aromatic Nucleophilic Substitution-Smiles Rearrangement-Denitrocyclization

被引：15

作者：

Sapegin, Alexander V. ^{[2
]}

Kalinin, Stanislav A. ^{[2
]}

Smirnov, Alexey V. ^{[2
]}

Dorogov, Mikhail V. ^{[2
]}

Krasavin, Mikhail ^{[1
]}

机构：

[1] Griffith Univ, Eskitis Inst Cell & Mol Therapies, Nathan, Qld 4111, Australia

[2] Ushinsky Yaroslavl State Pedag Univ, Yaroslavl 150000, Russia

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 15期

关键词：

tetracyclic scaffolds; privileged structures; atom-economical syntheses; dibenzo[b,f][1,4]oxazepines; Smiles rearrangement; nucleophilic aromatic substitution; denitrocyclization; regiospecific reaction; POTENT; DERIVATIVES;

D O I：

10.1055/s-0031-1289789

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethylformamide results in a tandem, atom-economical, aromatic nucleophilic substitution-Smiles rearrangement-denitrocyclization process to provide pyrazolo-fused dibenzo[b,f][1,4]oxazepines as a single regioisomer.

引用

页码：2401 / 2407

页数：7

共 3 条

[1] Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement
Hu, Fangdong
Liu, Huanhuan
Jia, Jiong
Ma, Chen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (47) : 11076 - 11079
[2] One Pot Regioselective Synthesis of a Small Library of Dibenzo[b,f][1,4]thiazepin-11(10H)-ones via Smiles Rearrangement
Zhao, Yongmei
Dai, Qiaoling
Chen, Zhi
Zhang, Qihui
Bai, Yongcheng
Ma, Chen
ACS COMBINATORIAL SCIENCE, 2013, 15 (02) : 130 - 134
[3] Synthesis of a new polycyclic heterocyclic ring system. Part III. Benzo[b] imidazo[1,5-d][1,4] oxazepine-1,4(2H, 5H)-diones
Stanisheva, Desislava V.
Gerova, Mariana S.
Petrov, Ognyan I.
HETEROCYCLIC COMMUNICATIONS, 2017, 23 (01) : 23 - 27

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