Efficient Generation of Highly Functionalized Fused Oxazepine Frameworks Based on a CAN-Catalyzed Four-Component Tetrahydropyridine Synthesis/Ring-Closing Metathesis Sequence

被引：35

作者：

Sridharan, Vellaisamy ^{[1
]}

Maiti, Swarupananda ^{[1
]}

Carlos Menendez, J. ^{[1
]}

机构：

[1] Univ Complutense, Dept Quim Organ & Farmaceut, Fac Farm, E-28040 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 24期

关键词：

CERIUM(IV) AMMONIUM-NITRATE; STEREOSELECTIVE-SYNTHESIS; 3-COMPONENT REACTION; ENYNE METATHESIS; POVAROV REACTION; VINYL ETHERS; DRUG DESIGN; PEPTIDOMIMETICS; 1,4-DIHYDROPYRIDINES; CONVENIENT;

D O I：

10.1021/jo9021309

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Allyl(propargyl)-6-allyl(propargyl)oxy-1,4,5,6-tetrahydropyridines, obtained through a CAN-catalyzed four-component reaction, were transformed into highly functionalized pyrido[2,1-b]-[1,3]oxazepines by ring-closing metathesis (RCM) and ring-closing enyne metathesis (RCEYM) processes, which constitute the first examples of the preparation of 1,3-oxazepine systems using metathesis reactions.

引用

页码：9365 / 9371

页数：7

共 38 条

[1] Peptidomimetics in cancer chemotherapy [J].

Avendano, C. ;

Menendez, J. C. .

CLINICAL & TRANSLATIONAL ONCOLOGY, 2007, 9 (09) :563-570

[2] REGIOCHEMISTRY IN THE SYNTHESIS OF 2,3,8,8A-TETRAHYDRO-7H-OXAZOLO[3,2-A]PYRIDINES [J].

CABALLERO, E ;

PUEBLA, P ;

MEDARDE, M ;

FELICIANO, AS .

TETRAHEDRON, 1993, 49 (44) :10079-10088

[3] Highly efficient synthesis of azabicyclo[x.y.0]alkane amino acids and congeners by means of Rh-catalyzed cyclohydrocarbonylation [J].

Chiou, Wen-Hua ;

Mizutani, Nobihiro ;

Ojima, Iwao .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :1871-1882

[4] Peptidomics in drug research [J].

Clynen, E. ;

Baggerman, G. ;

Husson, S. J. ;

Landuyt, B. ;

Schoofs, L. .

EXPERT OPINION ON DRUG DISCOVERY, 2008, 3 (04) :425-440

[5] HIGHLY REACTIVE AND STEREOSELECTIVE (R) AND (S)-3-(N,N-DIMETHYLCARBAMOYL)-1,2,4-TRIMETHYL-1,4-DIHYDROPYRIDINES FOR NADH NAD+ MIMICRY [J].

DEKOK, PMT ;

BASTIAANSEN, LAM ;

VANLIER, PM ;

VEKEMANS, JAJM ;

BUCK, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1313-1320

[6] Enyne metathesis (enyne bond reorganization) [J].

Diver, ST ;

Giessert, AJ .

CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382

[7]

ESTIARTE MA, 2003, BURGERS MED CHEM DRU, V1, P633

[8]

Giannis A., 1997, ADV DRUG RES, V29, P1

[9]

Goodman M, 2001, BIOPOLYMERS, V60, P229, DOI 10.1002/1097-0282(2001)60:3<229::AID-BIP10034>3.0.CO

[10]

2-P

← 1 2 3 4 →