A straightforward preparation of benzo[f]naphtho[b][1,4]oxazepines from TNT

被引：8

作者：

Samet, Alexander V. ^{[1
]}

Kislyi, Konstantine A. ^{[1
]}

Marshalkin, Victor N. ^{[1
]}

Strelenko, Yuri A. ^{[1
]}

Raihstat, Mikhail M. ^{[1
]}

Nelyubina, Yulia V. ^{[2
]}

Semenov, Victor. V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

TETRAHEDRON | 2008年 / 64卷 / 51期

关键词：

2,4,6-Trinitrotoluene; 1-Nitroso-2-naphthol; Benzo[f]naphtho[b][1,4]oxazepines; SNAr reactions;

D O I：

10.1016/j.tet.2008.09.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,4,6-Trinitrotoluene readily reacts with 1-nitroso-2-naphthol to afford 9,11-dinitrobenzo[f]naphtho[2,1-b][1,4]oxazepine. The nitro groups of the latter undergo displacement by O- and S-nucleophiles with preferential substitution of the 11-NO2 (peri-nitro group). The structures of the substitution products are confirmed by X-ray diffraction and H-1 NMR NOE experiments. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：11763 / 11767

页数：5

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