Concise syntheses of meridianins by carbonylative alkynylation and a four-component pyrimidine synthesis

被引：189

作者：

Karpov, AS ^{[1
]}

Merkul, E ^{[1
]}

Rominger, F ^{[1
]}

Müller, TJJ ^{[1
]}

机构：

[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 42期

关键词：

C-C coupling; carbonylation; heterocycles; multicomponent reactions; natural products;

D O I：

10.1002/anie.200501703

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) In one go: (Hetero)aryl iodides, alkynes, carbon monoxide, and amidines can be assembled in a consecutive four-component reaction to give pyrimidines by a sequence of carbonylative alkynylation and cyclocondensation. Carbonylative alkynylation also is the key step in the two-step syntheses of meridianins and meridianin derivatives. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6951 / 6956

页数：6

共 33 条

[1] Total syntheses of variolin B and deoxyvariolin B [J].

Ahaidar, A ;

Fernández, D ;

Danelón, G ;

Cuevas, C ;

Manzanares, I ;

Albericio, F ;

Joule, JA ;

Alvarez, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10020-10029

[2] Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia [J].

Ahmed, MSM ;

Mori, A .

ORGANIC LETTERS, 2003, 5 (17) :3057-3060

[3] Synthesis of deoxyvariolin B [J].

Alvarez, M ;

Fernández, D ;

Joule, JA .

TETRAHEDRON LETTERS, 2001, 42 (02) :315-317

[4]

[Anonymous], SOFTWARE PACKAGE SHE

[5]

ARCADI A, 1995, SYNLETT, P823

[6] Regioselective synthesis of 1,3,5-substituted pyrazoles from acetylenic ketones and hydrazines [J].

Bishop, BC ;

Brands, KMJ ;

Gibb, AD ;

Kennedy, DJ .

SYNTHESIS-STUTTGART, 2004, (01) :43-52

[7] RECENT PROGRESS IN BARBITURIC-ACID CHEMISTRY [J].

BOJARSKI, JT ;

MOKROSZ, JL ;

BARTON, HJ ;

PALUCHOWSKA, MH .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1985, 38 :229-297

[8]

Brown D. J., 1984, COMPREHENSIVE HETERO, V3

[9]

Brown D. J., 1970, CHEM HETEROCYCLIC CO, V16

[10] Specificity and mechanism of action of some commonly used protein kinase inhibitors [J].

Davies, SP ;

Reddy, H ;

Caivano, M ;

Cohen, P .

BIOCHEMICAL JOURNAL, 2000, 351 (351) :95-105

← 1 2 3 4 →