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

[81] Enantioselective total synthesis of (-)-heliannuol A [J].

Kishuku, H ;

Shindo, M ;

Shishido, K .

CHEMICAL COMMUNICATIONS, 2003, (03) :350-351

[82] NOVEL ANGIOTENSIN-II RECEPTOR ANTAGONISTS - DESIGN, SYNTHESIS, AND IN-VITRO EVALUATION OF DIBENZO[A,D]CYCLOHEPTENE AND DIBENZO[B,F]OXEPIN DERIVATIVES - SEARCHING FOR BIOISOSTERES OF BIPHENYLYLTETRAZOLE USING A 3-DIMENSIONAL SEARCH TECHNIQUE [J].

KIYAMA, R ;

HONMA, T ;

HAYASHI, K ;

OGAWA, M ;

HARA, M ;

FUJIMOTO, M ;

FUJISHITA, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2728-2741

[83] A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles [J].

Klapars, A ;

Antilla, JC ;

Huang, XH ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7727-7729

[84] Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed C-N bond formation - Ring-expansion process [J].

Klapars, A ;

Parris, S ;

Anderson, KW ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3529-3533

[85] Synthesis and SAR of N-substituted dibenzazepinone derivatives as novel potent and selective αvβ3 antagonists [J].

Kling, A ;

Backfisch, G ;

Delzer, R ;

Geneste, H ;

Graef, C ;

Holzenkamp, U ;

Hornberger, W ;

Lange, UEW ;

Lauterbach, A ;

Mack, H ;

Seitz, W ;

Subkowski, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (03) :441-446

[86] Novel synthesis of the pyrrolo[2,1-c][1,4]benzodiazocine ring system via a Dieckmann condensation [J].

Koriatopoulou, Konstantina ;

Karousis, Nikolaos ;

Varvounis, George .

TETRAHEDRON, 2008, 64 (42) :10009-10013

[87] Renaissance of Ullmann and Goldberg reactions - Progress in copper catalyzed C-N-, C-O- and C-S-coupling [J].

Kunz, K ;

Scholz, U ;

Ganzer, D .

SYNLETT, 2003, (15) :2428-2439

[88]

Kwong F. Y., 2002, ORG LETT, V4, P4

[89] Synthesis of medium-ring nitrogen heterocycles via palladium-catalyzed heteroannulation of 1,2-dienes [J].

Larock, RC ;

Tu, C ;

Pace, P .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6859-6866

[90] Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation [J].

Ley, SV ;

Thomas, AW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5400-5449

← 4 5 6 7 8 9 10 11 12 13 →