Synthesis of imidazo[1,5-a]quinoxalin-4(5H)-one template via a novel intramolecular cyclization process

被引：16

作者：

Norris, D ^{[1
]}

Chen, P ^{[1
]}

Barrish, JC ^{[1
]}

Das, J ^{[1
]}

Moquin, R ^{[1
]}

Chen, BC ^{[1
]}

Guo, P ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Pharmaceut Res Inst, Discovery Chem, Princeton, NJ 08543 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(01)00698-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, efficient, and regiospecific method for the construction of the imidazo[1,5-alpha ]quinoxalin-4(5H)-one template is described. The key reaction involves an intramolecular cyclization process and provides the desired products in excellent yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4297 / 4299

页数：3

共 11 条

[1]

[Anonymous], 1989, EP P., Patent No. 344943

[2] Pyrroloquinoxaline derivatives as high-affinity and selective 5-HT3 receptor agonists:: Synthesis, further structure-activity relationships, and biological studies [J].

Campiani, G ;

Morelli, E ;

Gemma, S ;

Nacci, V ;

Butini, S ;

Hamon, M ;

Novellino, E ;

Greco, G ;

Cagnotto, A ;

Goegan, M ;

Cervo, L ;

Dalla Valle, F ;

Fracasso, C ;

Caccia, S ;

Mennini, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4362-4379

[3] Reaction of quinoxalin-2-ones with TosMIC reagent:: synthesis of imidazo[1,5-a]quinoxalin-4-ones [J].

Chen, P ;

Barrish, JC ;

Iwanowicz, E ;

Lin, J ;

Bednarz, MS ;

Chen, BC .

TETRAHEDRON LETTERS, 2001, 42 (26) :4293-4295

[4]

COLLTTA V, 1995, EUR J MED CHEM, V30, P133

[5] NOVEL COMPOUNDS POSSESSING POTENT CAMP AND CGMP PHOSPHODIESTERASE INHIBITORY ACTIVITY - SYNTHESIS AND CARDIOVASCULAR EFFECTS OF A SERIES OF IMIDAZO[1,2-A]QUINOXALINONES AND IMIDAZO[1,5-A]QUINOXALINONES AND THEIR AZA ANALOGS [J].

DAVEY, DD ;

ERHARDT, PW ;

CANTOR, EH ;

GREENBERG, SS ;

INGEBRETSEN, WR ;

WIGGINS, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2671-2677

[6] DEHYDRATIVE DIMERIZATION OF 2- + 4-METHYL-5-IMIDAZOLECARBOXYLIC ACIDS [J].

GODEFROI, EF ;

VANDEWESTERINGH, C ;

VANDEREYCKEN, CAM .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (12) :3707-&

[7] 3-phenyl-substituted imidazo[1,5-a]quinoxalin-4-ones and imidazo[1,5-a]quinoxaline ureas that have high affinity at the GABA(A)/benzodiazepine receptor complex [J].

Jacobsen, EJ ;

Stelzer, LS ;

Belonga, KL ;

Carter, DB ;

Im, WB ;

Sethy, VH ;

Tang, AH ;

VonVoigtlander, PF ;

Petke, JD .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3820-3836

[8]

KASINA S, 1975, SYNTHESIS-STUTTGART, P162

[9]

Lee T.D., 1984, U.S. Patent 4,440,929, Patent No. 4440929

[10] 8-(1H-imidazol-1-yl)-7-nitro-4(5H)-imidazo[1,2-a]quinoxalinone and related compounds: Synthesis and structure-activity relationships for the AMPA-type non-NMDA receptor [J].

Ohmori, J ;

ShimizuSasamata, M ;

Okada, M ;

Sakamoto, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (13) :2053-2063

← 1 2 →