Gold-Catalyzed Regioselective Synthesis of Pyrazolo[1,4]oxazepines via Intramolecular7-endo-digCyclization

被引:11
作者
Thummala, Yadagiri [1 ,2 ]
Raju, Chittala Emmaniel [1 ,2 ]
Purnachandar, Dalovai [1 ,2 ]
Sreenivasulu, Gottam [1 ,2 ]
Doddi, Venkata Ramana [3 ]
Karunakar, Galla V. [1 ,2 ]
机构
[1] CSIR, Indian Inst Chem Technol, Fluoro & Agrochem Dept, Hyderabad 500007, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
[3] Cent Univ Karnataka, Dept Chem & Chem Sci, Kadaganchi 585367, Karnataka, India
关键词
Gold catalysis; 7-endo digCyclization; Pyrazolo[1; 4]Oxazepines; C-N bond formation; PROPARGYLIC BETA-ENAMINONES; INTRAMOLECULAR CYCLIZATION; ASYMMETRIC INDUCTION; FACILE FORMATION; DERIVATIVES; AMOXAPINE; DESIGN; ACIDS; ISOMERIZATION; ACHIEVEMENTS;
D O I
10.1002/ejoc.201901852
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient gold-catalyzed intramolecular regioselective synthesis of pyrazolo[1,4]oxazepines were developed from alkynyl-substituted pyrazoles via7-endo digcyclization. In this reaction a new C-N bond was formed and substituted pyrazolo[1,4]oxazepines were obtained in moderate to very good yields. Whereas alkynyl-substituted pyrazoles treated with sodium hydride produced the corresponding pyrazolo[1,4]oxazines regioselectively, via6-exo digcyclization in one-pot synthesis.
引用
收藏
页码:3560 / 3567
页数:8
相关论文
共 87 条
[1]   Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles:: a new entry to [1,4]oxazino[4,3-a]indoles [J].
Abbiati, G ;
Canevari, V ;
Caimi, S ;
Rossi, E .
TETRAHEDRON LETTERS, 2005, 46 (42) :7117-7120
[2]   Synthesis and structure-antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones [J].
Agirbas, Hikmet ;
Kemal, Berat ;
Budak, Fatma .
MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (08) :1170-1180
[3]  
[Anonymous], 2009, Angew. Chem
[4]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[5]  
Balani N. D., 1995, Indian Journal of Physiology and Pharmacology, V39, P293
[6]   SYSTEMATIC STUDIES WITH AMOXAPINE, A NEW ANTI-DEPRESSANT [J].
BAN, TA ;
FUJIMORI, M ;
PETRIE, WM ;
RAGHEB, M ;
WILSON, WH .
INTERNATIONAL PHARMACOPSYCHIATRY, 1982, 17 (01) :18-27
[7]   ` Intramolecular Gold-Catalyzed and NaH-Supported Cyclization Reactions of N-Propargyl Indole Derivatives with Pyrazole and Pyrrole Rings: Synthesis of Pyrazolodiazepinoindole, Pyrazolopyrazinoindole, and Pyrrolopyrazinoindole [J].
Basceken, Sinan ;
Kaya, Serdal ;
Balci, Metin .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12552-12561
[8]   Design of Pyrazolo-pyrrolo-pyrazines and Pyrazolo-pyrrolo-diazepines via AuCl3-Catalyzed and NaH-Supported Cyclization of N-Propargyl Pyrazoles [J].
Basceken, Sinan ;
Balci, Metin .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) :3806-3814
[9]   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
[10]   TREATMENT ADHERENCE [J].
BLACKWELL, B .
BRITISH JOURNAL OF PSYCHIATRY, 1976, 129 (DEC) :513-&