A facile access to the 1,5-dihydro- and 1,3,4,5-tetrahydro-benzo[b]azepin-2-one ring systems via a new ring enlargement

被引：0

作者：

Pauvert, M ^{[1
]}

Dupont, V ^{[1
]}

Guingant, A ^{[1
]}

机构：

[1] Fac Sci & Tech, Synth Organ Lab, F-44322 Nantes 03, France

来源：

SYNLETT | 2002年 / 08期

关键词：

quinolinium salt; silver nitrate; 1,5-dihydro-benzo[b]azepin-2-one; 1,3,4,5-tetrahydro-benzo[b] azepin-2-one; ring enlargement;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of a 1,5-dihydro-benzo[b]azepin-2-one is reported. The key reaction is a silver nitrate-induced rearrangement of N-benzyl quinolinium bromide. Its reduction leads to the 1,3,4,5-tetrahydro-benzo[b] azepin-2-one ring system found in several pharmacological important compounds.

引用

页码：1350 / 1352

页数：3

共 50 条

[31] Synthesis and X-ray diffraction data of 6,8-dimethyl-cis-2-vinyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol and 8-chloro-9-methyl-cis-2-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol
Macias, M. A.
Henao, J. A.
Maria Acosta, Lina
Palma, Alirio
POWDER DIFFRACTION, 2011, 26 (04) : 346 - 349
[32] RING ENLARGEMENT OF 2-OXO-1,3-DITHIANE - EASY ACCESS TO 4-SUBSTITUTED-7,8-DIHYDRO-2H,6H-1,5-DITHIOCIN-2-ONE
FOURNET, G
GORE, J
TETRAHEDRON LETTERS, 1993, 34 (44) : 7057 - 7058
[33] A rapid and facile method for the general synthesis of 3-aryl substituted 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazines and their ring fused analogues
Chowdhury, Chinmay
Mukherjee, Sanjukta
Chakraborty, Biswajit
Achari, Basudeb
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (16) : 5856 - 5862
[34] Synthesis of benzo[d]benzo[2,3][1,4]diazepino[1,7-(b)under-bar]isothiazole, a new heterocyclic ring system
Bassin, JP
Frearson, MJ
Al-Nawwar, K
SYNTHETIC COMMUNICATIONS, 2000, 30 (16) : 2961 - 2965
[35] SUBSTITUTED BICYCLIC AND TRICYCLIC OXAZOLO[4,5-D]-1,2,3-TRIAZOLE SYSTEMS - RING EXPANSIONS TO 1,3,4,5-OXATRIAZINES AND RING CONTRACTIONS TO 1,2,3-TRIAZASPIROALKANE DERIVATIVES
BUTLER, RN
OSHEA, DF
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19): : 2797 - 2800
[36] Synthesis and spectroscopic characterisation of 4,5-dihydro-[1,2,3]triazolo[5,1-f][1,2,4]triazines. A novel condensed heterocyclic ring system
Laskos, E
Lianis, PS
Rodios, NA
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (03) : 599 - 604
[37] Ring enlargement reaction of 3-hydroxy-3-propargylisoindolin-1-ones: A new synthetic method for the 2-benzazepine-1,5-diones
Nagao, Y
Jeong, IY
Lee, WS
TETRAHEDRON LETTERS, 1996, 37 (03) : 393 - 396
[38] RESEARCH IN FIELD OF 2,3-DIHYDRO-1H-BENZO(B)CYCLOPENTA(D)SELENOPHENE,1,2,3,4-TETRAHYDRODIBENZOSELENOPHENE AND 2,3,4,5-TETRAHYDRO-1H-BENZO(B)CYCLOPENTA(D)SELENOPHENE
CAGNIANT, P
KIRSCH, G
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1971, 272 (24): : 1978 - &
[39] On triazoles -: XLIV.: Synthesis of new ring systems containing imidazo[2′,1′:3,4][1,2,4]triazolo[1,5-a]pyrimidine and imidazo[1′,2′:2,3][1,2,4]triazolo[1,5-a]pyrimidine skeleton
Berecz, G
Reiter, J
Argay, G
Kálmán, A
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (02) : 319 - 325
[40] THIENO[2',3'/3,4]PYRAZOLO[1,5-A]PYRIMIDINES AND THIENO[2',3'/3,4]PYRAZOLO[1,5-A]TRIAZINES - SYNTHESIS OF THE NOVEL RING-SYSTEMS
BRIEL, D
PHARMAZIE, 1995, 50 (10): : 675 - 678

← 1 2 3 4 5 →