Stereoselective Synthesis of Novel Highly Substituted Isochromanone and Isoquinolinone-Containing Exocyclic Tetrasubstituted Alkenes

被引：25

作者：

Arthuis, Martin

Pontikis, Renee ^{[1
]}

Florent, Jean-Claude

机构：

[1] Inst Curie, Ctr Rech, F-75248 Paris 05, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 05期

关键词：

PALLADIUM; CYCLIZATION; HETEROCYCLES; DERIVATIVES; ANALOGS;

D O I：

10.1021/jo802729s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthetic route toward the synthesis of highly substituted arylethylidene-isoquinolinones/isochromanones is reported. The tandem carbopalladation/Suzuki-Miyaura coupling sequence stereoselectively provided various functionalized polycyclic compounds in moderate to excellent yields.

引用

收藏

页码：2234 / 2237

页数：4

相关论文

共 29 条

[1] Tandem Heck-Suzuki-Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4 [J].

Arthuis, Martin ;

Pontikis, Renee ;

Florent, Jean-Claude .

TETRAHEDRON LETTERS, 2007, 48 (36) :6397-6400

[2] 4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids:: Synthesis and evaluation as anti-mitotic and cytotoxic agents [J].

Banwell, MG ;

Hamel, E ;

Hockless, DCR ;

Verdier-Pinard, P ;

Willis, AC ;

Wong, DJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (13) :4627-4638

[3] Copper-mediated N-cyclopropylation of azoles, amides, and sulfonamides by cyclopropylboronic acid [J].

Benard, Sebastien ;

Neuville, Luc ;

Zhu, Jieping .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16) :6441-6444

[4] A CONVENIENT SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLIN-3-ONES AND EVIDENCE FOR THE PARTICIPATION OF A QUINONE METHIDE INTERMEDIATE IN THE THERMOLYSIS OF MIXTURES OF ISOCHROMAN-3-ONES AND UREAS [J].

BLACK, GG ;

SAINSBURY, M ;

MAJEED, AJ .

TETRAHEDRON, 1984, 40 (21) :4383-4386

[5]

BROWN HC, 1981, SYNTHESIS-STUTTGART, P605

[6] REGIOSPECIFIC PALLADIUM CATALYZED TANDEM CYCLISATION-ANION CAPTURE PROCESSES - STEREOSPECIFIC GROUP TRANSFER FROM ORGANOZINC AND ORGANOBORON REAGENTS [J].

BURNS, B ;

GRIGG, R ;

SRIDHARAN, V ;

STEVENSON, P ;

SUKIRTHALINGAM, S ;

WORAKUN, T .

TETRAHEDRON LETTERS, 1989, 30 (09) :1135-1138

[7]

Cherkaoui MZ, 1997, NEW J CHEM, V21, P1203

[8] A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].

Cheung, WS ;

Patch, RJ ;

Player, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744

[9] DIASTEREOSELECTIVITY IN NUCLEOPHILIC-ADDITION REACTIONS TO (ALPHA-BETA-DIALKOXYACYL)SILANES - AN OPERATIONALLY USEFUL ROUTE TO OPTICALLY-ACTIVE 1,2,3-SYN-TRIOLS [J].

CIRILLO, PF ;

PANEK, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6071-6073

[10] Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].

Couty, S ;

Liégault, B ;

Meyer, C ;

Cossy, J .

ORGANIC LETTERS, 2004, 6 (15) :2511-2514