One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones by a Smiles Rearrangement

被引:8
作者
Jiang, Xiaolei [1 ]
Hu, Fangdong [1 ]
机构
[1] Linyi Univ, Sch Chem & Chem Engn, Linyi 276005, Shandong, Peoples R China
关键词
indoles; indolopyridazinobenzoxazepinanes; regioselectivity; polycyclic heterocycles; Smiles rearrangement; DIBENZOXAZEPINONES; CONSTRUCTION;
D O I
10.1055/s-0037-1609338
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and convenient synthesis of indole-fused pyridazino[4,5-b][1,4]benzoxazepin-4(3H)-ones is described. A range of 2-(1Hindol-2-yl)phenols and 4,5-dichloropyridazln-3-ones are compatible with this reaction. A Smiles rearrangement is proposed as a key step in the highly regioselective construction of the products. The easy availability of the starting materials makes this an appealing method in organic synthesis.
引用
收藏
页码:1207 / 1210
页数:4
相关论文
共 25 条
[1]   Antiproliferative and Differentiating Activities of a Novel Series of Histone Deacetylase Inhibitors [J].
Binaschi, Monica ;
Boldetti, Andrea ;
Gianni, Maurizio ;
Maggi, Carlo Alberto ;
Gensini, Martina ;
Bigioni, Mario ;
Parlani, Massimo ;
Giolitti, Alessandro ;
Fratelli, Maddalena ;
Valli, Claudia ;
Terao, Mineko ;
Garattini, Enrico .
ACS MEDICINAL CHEMISTRY LETTERS, 2010, 1 (08) :411-415
[2]   An efficient synthesis of [1,4]pyridazinooxazine[3,4-a]tetrahydro isoquinolines [J].
Cho, SD ;
Park, YD ;
Kim, JJ ;
Joo, WH ;
Shiro, M ;
Esser, L ;
Falck, JR ;
Ahn, CJ ;
Shin, DS ;
Yoon, YJ .
TETRAHEDRON, 2004, 60 (17) :3763-3773
[3]   A one-pot synthesis of pyrido[2,3-b][1,4]oxazin-2-ones [J].
Cho, SD ;
Park, YD ;
Kim, JJ ;
Lee, SG ;
Ma, C ;
Song, SY ;
Joo, WH ;
Falck, JR ;
Shiro, M ;
Shin, DS ;
Yoon, YJ .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7918-7920
[4]   Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones [J].
Cho, SD ;
Song, SY ;
Park, YD ;
Kim, JJ ;
Joo, WH ;
Shiro, M ;
Falck, JR ;
Shin, DS ;
Yoon, YJ .
TETRAHEDRON LETTERS, 2003, 44 (50) :8995-8998
[5]   SAR study of 2,3,4,14b-tetrahydro-1H-dibenzo[b,f] pyrido[ 1,2-d][1,4] oxazepines as progesterone receptor agonists [J].
Dols, Paul P. M. A. ;
Folmer, Brigitte J. B. ;
Hamersma, Hans ;
Kuil, Cor W. ;
Lucas, Hans ;
Ollero, Lourdes ;
Rewinkel, Jos B. M. ;
Hermkens, Pedro H. H. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (04) :1461-1467
[6]   Design, synthesis and SAR of phenylamino-substituted 5,11-dihydro-dibenzo[a,d]cyclohepten-10-ones and 11H-dibenzo[b,f]oxepin-10-ones as p38 MAP kinase inhibitors [J].
Dorn, Angelika ;
Schattel, Verena ;
Laufer, Stefan .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (10) :3074-3077
[7]   Analogues of Morphanthridine and the Tear Gas Dibenz[b,f][1,4]oxazepine (CR) as Extremely Potent Activators of the Human Transient Receptor Potential Ankyrin1 (TRPA1) Channel [J].
Gijsen, Harrie J. M. ;
Berthelot, Didier ;
Zaja, Mirko ;
Brone, Bert ;
Geuens, Ivo ;
Mercken, Marc .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :7011-7020
[8]   8-CHLORODIBENZ[B,F][1,4]OXAZEPINE-10(11H)-CARBOXYLIC ACID, 2-[3-[2-(FURANYLMETHYL)THIO]-1-OXOPROPYL]HYDRAZIDE (SC-51322) - A POTENT PGE(2) ANTAGONIST AND ANALGESIC [J].
HALLINAN, EA ;
STAPELFELD, A ;
SAVAGE, MA ;
REICHMAN, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (03) :509-514
[9]   Copper-Catalyzed Cross-Coupling Interrupted by an Opportunistic Smiles Rearrangement: An Efficient Domino Approach to Dibenzoxazepinones [J].
Kitching, Matthew O. ;
Hurst, Timothy E. ;
Snieckus, Victor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) :2925-2929
[10]   Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety [J].
Kochanowska-Karamyan, Anna J. ;
Hamann, Mark T. .
CHEMICAL REVIEWS, 2010, 110 (08) :4489-4497