2,3-Disubstituted pyrrolo[2,3-b]quinoxalines via aminopalladation-reductive elimination

被引:30
作者
Arcadi, A
Cacchi, S
Fabrizi, G
Parisi, LM
机构
[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biologi, I-00185 Rome, Italy
[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, Fac Sci, I-67100 Laquila, Italy
关键词
quinoxalines; alkynes; palladium; cyclization; aminopalladation-reductive; elimination;
D O I
10.1016/j.tetlet.2004.01.058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,3-Disubstituted pyrrolo[2,3-b]quinoxalines have been prepared in good to high yield through the reaction of 2-alkynyl-3-trifluoroacetamidoquinoxalines with aryl and vinyl halides or triflates in the presence of Pd(PPh3)(4) and K2CO3 in MeCN at 100 degreesC. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2431 / 2434
页数:4
相关论文
共 22 条
  • [1] AMES DE, 1985, J CHEM RES, P144
  • [2] Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671
  • [3] Pyrroloquinoxaline derivatives as high-affinity and selective 5-HT3 receptor agonists:: Synthesis, further structure-activity relationships, and biological studies
    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
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) : 4362 - 4379
  • [4] Novel and highly potent 5-HT3 receptor agonists based on a pyrroloquinoxaline structure
    Campiani, G
    Cappelli, A
    Nacci, V
    Anzini, M
    Vomero, S
    Hamon, M
    Cagnotto, A
    Fracasso, C
    Uboldi, C
    Caccia, S
    Consolo, S
    Mennini, T
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) : 3670 - 3678
  • [5] David R, 1998, Expert Opin Investig Drugs, V7, P1063, DOI 10.1517/13543784.7.7.1063
  • [6] 4-(2,2-dimethyldioxalan-4-yl)-5-(quinoxalin-2-yl)-1,3-dithiol-2-one, a proligand relating to the cofactor of the oxomolybdoenzymes
    Dinsmore, A
    Garner, CD
    Joule, JA
    [J]. TETRAHEDRON, 1998, 54 (13) : 3291 - 3302
  • [7] THE MECHANISM OF ACTION OF THE ANTI-HERPES VIRUS COMPOUND 2,3-DIMETHYL-6(2-DIMETHYLAMINOETHYL)-6H-INDOLO-(2,3-B)QUINOXALINE
    HARMENBERG, J
    AKESSONJOHANSSON, A
    GRASLUND, A
    MALMFORS, T
    BERGMAN, J
    WAHREN, B
    AKERFELDT, S
    LUNDBLAD, L
    COX, S
    [J]. ANTIVIRAL RESEARCH, 1991, 15 (03) : 193 - 204
  • [8] SYNTHESIS OF 9-(TRIFLUOROMETHYL)PYRIDO[1',2'/1,2]-IMIDAZO[4,5-B]QUINOXALINES
    IWATA, S
    SAKAJYO, M
    TANAKA, K
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (06) : 1433 - 1438
  • [9] Synthesis of 4-(1-dialkylaminoalkyl)pyrrolo[1,2-a]quinoxalines
    Kobayashi, K
    Matsumoto, T
    Irisawa, S
    Yoneda, K
    Morikawa, O
    Konishi, H
    [J]. HETEROCYCLES, 2001, 55 (05) : 973 - 980
  • [10] Synthesis of pyrrolo[1,2-a]quinoxaline and its 4-(1-hydroxyalkyl) derivatives by Lewis acid-catalyzed reactions of 1-(2-isocyanophenyl)pyrrole
    Kobayashi, K
    Matoba, T
    Irisawa, S
    Matsumoto, T
    Morikawa, O
    Konishi, H
    [J]. CHEMISTRY LETTERS, 1998, (06) : 551 - 552