Regioselective formation of medium-ring heterocycles of biological relevance by intramolecular cyclization

被引：90

作者：

Majumdar, K. C. ^{[1
,2
]}

机构：

[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

[2] Tezpur Univ, Dept Chem Sci, Tezpur 784028, Assam, India

来源：

RSC ADVANCES | 2011年 / 1卷 / 07期

关键词：

PALLADIUM-CATALYZED ARYLATION; CONSTRAINED PHENYLALANINE DERIVATIVES; ENANTIOSELECTIVE TOTAL-SYNTHESIS; N BOND FORMATION; HECK REACTION; RADICAL CYCLIZATION; CLAISEN REARRANGEMENT; EFFICIENT SYNTHESIS; ARYL HALIDES; CYCLIC SULFONAMIDES;

D O I：

10.1039/c1ra00494h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This brief account describes our progress on the regioselective synthesis of medium-sized heterocycles. Formation of the medium-ring (seven-, eight-, nine-membered) oxa-, aza-, thia, oxa-thia- and aza-thia-heterocycles has been achieved by the intramolecular metal-mediated cyclization (especially Pd-catalyzed), diene and enyne metathesis, thiol-mediated cyclization, iodocyclization and azide-alkyne cycloaddition.

引用

页码：1152 / 1170

页数：19

共 197 条

[1] Design and synthesis of novel scaffolds for drug discovery:: Hybrids of β-D-glucose with 1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-one, the corresponding 1-oxazepine, and 2-and 4-pyridyldiazepines [J].

Abrous, L ;

Hynes, J ;

Friedrich, SR ;

Smith, AB ;

Hirschmann, R .

ORGANIC LETTERS, 2001, 3 (07) :1089-1092

[2] A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization [J].

Aillaud, I ;

Bossharth, E ;

Conreaux, D ;

Desbordes, P ;

Monteiro, N ;

Balme, G .

ORGANIC LETTERS, 2006, 8 (06) :1113-1116

[3] Cyclization versus Pd-H elimination-readdition: Skeletal rearrangement of the products of Pd-C6F5 addition to 1,4-pentadienes [J].

Albeniz, AC ;

Espinet, P ;

Lin, YS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7145-7152

[4] Novel carbonyl bromoallylation/Heck reaction sequence.: Stereocontrolled access to bicyclic β-lactams [J].

Alcaide, B ;

Almendros, P ;

Rodríguez-Acebes, R .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2713-2719

[5] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].

ALVAREZ, R ;

VELAZQUEZ, S ;

SANFELIX, A ;

AQUARO, S ;

DECLERCQ, E ;

PERNO, CF ;

KARLSSON, A ;

BALZARINI, J ;

CAMARASA, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194

[6] Stereoselective synthesis of substituted 2,5-diazabicyclo[2.2.1]heptanes by iodine-mediated cyclization of optically pure compounds containing the 4,5-diamino-1,7-octadiene and 1,2-diamino-4-alkene moieties [J].

Alvaro, Giuseppe ;

Di Fabio, Romano ;

Gualandi, Andrea ;

Morelli, Claudio ;

Monari, Magda ;

Savoia, Diego ;

Zoli, Luca .

TETRAHEDRON, 2007, 63 (50) :12446-12453

[7] A simple, two-step synthesis of 3-iodoindoles [J].

Amjad, M ;

Knight, DW .

TETRAHEDRON LETTERS, 2004, 45 (03) :539-541

[8] Synthesis of a new series of 1,4-benzodiazepin-5-ones from cyanoester epoxides [J].

Ammadi, F ;

Boukhris, S ;

Souizi, A ;

Coudert, G .

TETRAHEDRON LETTERS, 1999, 40 (36) :6517-6518

[9] Synthesis of sulphur-containing heterocycles by ring closing diene metathesis [J].

Armstrong, SK ;

Christie, BA .

TETRAHEDRON LETTERS, 1996, 37 (52) :9373-9376

[10] Synthesis of medium ring heterocycles using an intramolecular Heck reaction [J].

Arnold, LA ;

Luo, WC ;

Guy, RK .

ORGANIC LETTERS, 2004, 6 (17) :3005-3007

← 1 2 3 4 5 6 7 8 9 10 →