General microwave-assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines

被引：244

作者：

Zhao, ZJ ^{[1
]}

Wisnoski, DD ^{[1
]}

Wolkenberg, SE ^{[1
]}

Leister, WH ^{[1
]}

Wang, Y ^{[1
]}

Lindsley, CW ^{[1
]}

机构：

[1] Merck Sharp & Dohme Ltd, Res Labs, Technol Enable Synth Grp, Dept Med Chem, W Point, PA 19486 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 25期

关键词：

microwave; quinoxaline; pyrazine;

D O I：

10.1016/j.tetlet.2004.04.144

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized quinoxalines and heterocyclic pyrazines are expediently prepared in excellent yields (69-99%) from common 1,2-diketone intermediates under microwave irradiation. In addition to being general for a variety of aryl/heteroaryl 1,2-diamines and 1,2-diketones, this protocol suppresses the formation of polymeric species, characteristic of traditional thermal conditions. (C) 2004 Published by Elsevier Ltd.

引用

页码：4873 / 4876

页数：4

共 17 条

[1] Brown D. J., 2004, CHEM HETEROCYCLIC CO
[2] Furka A, 2002, DRUG DISCOV TODAY, V7, P1
[3] Microwave-assisted ring-closing metathesis revisited. On the question of the nonthermal microwave effect
Garbacia, S
Desai, B
Lavastre, O
Kappe, CO
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) : 9136 - 9139
[4] Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 2: The synthesis and biological activities of RPR127963 an orally bioavailable inhibitor
He, W
Myers, MR
Hanney, B
Spada, AP
Bilder, G
Galzcinski, H
Amin, D
Needle, S
Page, K
Jayyosi, Z
Perrone, MH
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (18) : 3097 - 3100
[5] Katritzky A.R., 2010, HDB HETEROCYCLIC CHE, V3rd
[6] SOME SUBSTITUTED PYRIDO(2,3)PYRAZINES
KAYE, IA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (02) : 240 - &
[7] Thieno[3,4-b]pyrazines:: Synthesis, structure, and reactivity
Kenning, DD
Mitchell, KA
Calhoun, TR
Funfar, MR
Sattler, DJ
Rasmussen, SC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) : 9073 - 9076
[8] Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues
Kim, YB
Kim, YH
Park, JY
Kim, SK
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) : 541 - 544
[9] Development of a custom high-throughput preparative liquid chromatography/mass spectrometer platform for the preparative purification and analytical analysis of compound libraries
Leister, W
Strauss, K
Wisnoski, D
Zhao, ZJ
Lindsley, C
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (03): : 322 - 329
[10] Microwave assisted organic synthesis -: a review
Lidström, P
Tierney, J
Wathey, B
Westman, J
[J]. TETRAHEDRON, 2001, 57 (45) : 9225 - 9283

← 1 2 →