A divergent approach to highly substituted benzothiepinones and to 2,3-dihydrothieno[2,3-b]thiopyran-4-ones

被引：15

作者：

Boutillier, Peter ^{[1
]}

Quiclet-Sire, Beatrice ^{[1
]}

Zafar, Syeda Nahid ^{[1
]}

Zard, Samir Z. ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Lab Synth Organ Associe, F-91128 Palaiseau, France

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 13-14期

关键词：

REGIOSELECTIVE SYNTHESIS; ALKYLATIVE CYCLIZATION; SMOKING-CESSATION; DERIVATIVES; INHIBITORS; REARRANGEMENT; FACILE; AGENTS; HETEROCYCLES; DISCOVERY;

D O I：

10.1016/j.tetasy.2010.06.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The radical addition-transfer of S-(2-fluoro-phenacyl)xanthates can be used to construct rapidly benzothiepinones, including libraries of complex aza-bridged derivatives, and highly functionalized 2,3-dihydrothieno[2,3-b]thiopyran-4-ones. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1649 / 1665

页数：17

共 36 条

[1] ALDOL CONDENSATION OF EVANS CHIRAL ENOLATES WITH ACETOPHENONES - ITS APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF HOMOCHIRAL ANTIFUNGAL AGENTS [J].

BARTROLI, J ;

TURMO, E ;

BELLOC, J ;

FORN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3000-3012

[2] Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3,4,5,6-hexahydro-1,5-methano-3-benzazocine [J].

Bashore, Crystal G. ;

Vetelino, Michael G. ;

Wirtz, Michael C. ;

Brooks, Paige R. ;

Frost, Heather N. ;

McDermott, Ruth E. ;

Whritenour, David C. ;

Ragan, John A. ;

Rutherford, Jennifer L. ;

Makowski, Teresa W. ;

Brenek, Steven J. ;

Coe, Jotham W. .

ORGANIC LETTERS, 2006, 8 (26) :5947-5950

[3]

BOGESO KP, 1991, J MED CHEM, V34, P2023

[4] An expedient radical based approach to difluorophosphonate analogues of thionucleosides [J].

Boivin, J ;

Ramos, L ;

Zard, SZ .

TETRAHEDRON LETTERS, 1998, 39 (38) :6877-6880

[5] An unusual and highly efficient access to thieno[2,3-b]-benzothiopyran structures [J].

Boivin, J ;

Boutillier, P ;

Zard, SZ .

TETRAHEDRON LETTERS, 1999, 40 (13) :2529-2532

[6] A new radical-ionic allylation sequence [J].

Briggs, ME ;

Zard, SZ .

SYNLETT, 2005, (02) :334-336

[7] New antipsychotic agents with serotonin and dopamine antagonist properties based on a pyrrolo[2,1-b][1,3]benzothiazepine structure [J].

Campiani, G ;

Nacci, V ;

Bechelli, S ;

Ciani, SM ;

Garofalo, A ;

Fiorini, I ;

Wikström, H ;

de Boer, P ;

Liao, Y ;

Tepper, PG ;

Cagnotto, A ;

Mennini, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (20) :3763-3772

[8] In pursuit of α4β2 nicotinic receptor partial agonists for smoking cessation:: Carbon analogs of (-)-cytisine [J].

Coe, JW ;

Vetelino, MG ;

Bashore, CG ;

Wirtz, MC ;

Brooks, PR ;

Arnold, EP ;

Lebel, LA ;

Fox, CB ;

Sands, SB ;

Davis, TI ;

Schulz, DW ;

Rollema, H ;

Tingley, FD ;

O'Neill, BT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :2974-2979

[9] Varenicline:: An α4β2 nicotinic receptor partial agonist for smoking cessation [J].

Coe, JW ;

Brooks, PR ;

Vetelino, MG ;

Wirtz, MC ;

Arnold, EP ;

Huang, JH ;

Sands, SB ;

Davis, TI ;

Lebel, LA ;

Fox, CB ;

Shrikhande, A ;

Heym, JH ;

Schaeffer, E ;

Rollema, H ;

Lu, Y ;

Mansbach, RS ;

Chambers, LK ;

Rovetti, CC ;

Schulz, DW ;

Tingley, FD ;

O'Neill, BT .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (10) :3474-3477

[10] REDUCTIVE CLEAVAGE AND RING EXPANSION OF THIOCHROMANE AND BENZODIHYDROTHIOPHENE [J].

COHEN, T ;

CHEN, FP ;

KULINSKI, T ;

FLORIO, S ;

CAPRIATI, V .

TETRAHEDRON LETTERS, 1995, 36 (25) :4459-4462

← 1 2 3 4 →