A facile synthesis of benzo[b][1,4]thiazepine derivatives by palladium acetate catalyzed reaction

被引：13

作者：

Kaishap, Partha Pratim ^{[1
]}

Shekarrao, Kommuri ^{[1
]}

Saikia, Pallabi ^{[1
]}

Gogoi, Sanjib ^{[1
]}

Boruah, Romesh C. ^{[1
]}

机构：

[1] North East Inst Sci & Technol, Div Med Chem, Jorhat 785006, Assam, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 11期

关键词：

Benzo[b][1,4]thiazepine; Steroid; Palladium acetate; beta-Bromovinyl aldehyde; 2-Aminothiophenol; 1,3-DIPOLAR CYCLOADDITION; 1,5-BENZOTHIAZEPINES; QUINOLINES; PYRIDINE; SOLVENT;

D O I：

10.1016/j.tetlet.2014.01.153

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of steroid/nonsteroid fused benzo[b][1,4]thiazepines and 2-arylsubstituted benzo[b][1,4] thiazepines is described from Pd(OAc)(2) catalyzed reaction of steroidal/nonsteroidal beta-halovinyl aldehydes and 2-aminothiophenols in DMF under heating condition. (c) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1927 / 1930

页数：4

共 22 条

[1] Synthesis and biological evaluation of some nitrogen containing steroidal heterocycles [J].

Abdelhalim, Mervat M. ;

Kamel, Eman M. ;

Rabie, Samira T. ;

Mohamed, Nadia R. .

STEROIDS, 2011, 76 (1-2) :78-84

[2] Anti-inflammatory profile of some synthesized heterocyclic pyridone and pyridine derivatives fused with steroidal structure [J].

Amr, Abdel-Galil E. ;

Abdulla, Mohamed M. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (13) :4341-4352

[3] The expedient synthesis of 1,5-benzothiazepines as a family of cytotoxic drugs [J].

Arya, Kapil ;

Dandia, Anshu .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (01) :114-119

[4] 1,5-Benzothiazepine, a versatile pharmacophore: A review [J].

Bariwal, Jitender B. ;

Upadhyay, Kuldip D. ;

Manvar, Atul T. ;

Trivedi, Jalpa C. ;

Singh, Jyoti S. ;

Jain, Kishor S. ;

Shah, Anarmik K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (11) :2279-2290

[5] Palladium-catalyzed C-N bond formation:: synthesis of 1-aryl-1H-pyrazoles from β-bromovinyl aldehydes and arylhydrazines [J].

Cho, Chan Sik ;

Patel, Daksha B. .

TETRAHEDRON, 2006, 62 (26) :6388-6391

[6] Synthesis of 1,5-benzothiazepine derivatives bearing 2-phenoxy-quinoline moiety via 1,3-diplolar cycloaddition reaction [J].

Dong, Zhi-Qiang ;

Liu, Fang-Ming ;

Xu, Feng ;

Yuan, Zai-Liang .

MOLECULAR DIVERSITY, 2011, 15 (04) :963-970

[7] E-ring modified steroids as novel potent inhibitors of 17β-hydroxysteroid dehydrogenase type 1 [J].

Fischer, DS ;

Allan, GM ;

Bubert, C ;

Vicker, N ;

Smith, A ;

Tutill, HJ ;

Purohit, A ;

Wood, L ;

Packham, G ;

Mahon, MF ;

Reed, MJ ;

Potter, BVL .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (18) :5749-5770

[8] A microwave promoted solvent-free approach to steroidal quinolines and their in vitro evaluation for antimicrobial activities [J].

Gogoi, Shyamalee ;

Shekarrao, Kommuri ;

Duarah, Aparajita ;

Bora, Tarun C. ;

Gogoi, Sanjib ;

Boruah, Romesh C. .

STEROIDS, 2012, 77 (13) :1438-1445

[9] SYNTHESIS + STRUCTURE OF STEROIDAL PREGN-4-ENO- + 5ALPHA-PREGNANO(3,2-C)PYRAZOLES . NOVEL CLASS OF POTENT ANTI-INFLAMMATORY STERIODS [J].

HIRSCHMANN, R ;

BUCHSCHACHER, P ;

TISHLER, M ;

ELLIS, R ;

STEINBERG, NG ;

FRIED, JH ;

KENT, GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (08) :1520-&

[10] A facile synthesis and highly atom economic 1,3-dipolar cycloaddition of hexahydropyrido[3,4-c][1,5]benzothiazepines with nitrile oxide:: stereoselective formation of hexahydro[1,2,4]oxadiazolo[5,4-d]pyrido[3,4-c][1,5]benzothiazepines [J].

Kumar, Raju Ranjith ;

Perumal, Subbu .

TETRAHEDRON, 2007, 63 (33) :7850-7857

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