Organometallic alkylation of 2-chloro-4,6-dimethoxy-1,3,5-triazine: a study

被引：20
|
作者：
Samaritani, S [1 ]
Signore, G [1 ]
Malanga, C [1 ]
Menicagli, R [1 ]
机构：
[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
来源：
TETRAHEDRON | 2005年 / 61卷 / 18期
关键词：
2-chloro-4,6-diniethoxy-1,3,5-triazine; organometallics; coupling reactions; palladium and nickel catalysts;
D O I：
10.1016/j.tet.2005.02.085
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactivity of 2-chloro-4,6-dimethoxy-1,3,5-triazine (1) has been investigated in Pd- or Ni-catalyzed cross-coupling processes with organostannanes, Grignard reagents, organoalanes and organozinc halides. All organometallic reagents considered form new C-C bonds on the heteroaromatic ring and afford the corresponding 2-alkyl-4,6-dimethoxy-1,3,5-triazines in moderate to very good yields. The collected data allows the choice of the alkylating agent as well as the experimental conditions depending on the residue to transfer. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4475 / 4483
页数：9
相关论文
共 50 条
  • [1] 2-chloro-4,6-dimethoxy-1,3,5-triazine
    Fridman, N
    Kapon, M
    Kaftory, M
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2003, 59 (12) : O685 - O686
  • [2] Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine
    Sukiennik, Jaroslaw
    Kasperowicz-Frankowska, Katarzyna
    Szczesio, Malgorzata
    Fraczyk, Justyna
    Kolesinska, Beata
    Kaminski, Zbigniew J.
    ARKIVOC, 2021, : 85 - 98
  • [3] A study on the activation of carboxylic acids by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 2-chloro-4,6-diphenoxy-1,3,5-triazine
    Kaminski, ZJ
    Paneth, P
    Rudzinski, J
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13): : 4248 - 4255
  • [4] Application of 2-chloro-4,6-dimethoxy-1,3,5-triazine in the synthesis of 2-azetidinones
    Arnoosh Khademi Shiraz
    Maaroof Zarei
    Monatshefte für Chemie - Chemical Monthly, 2015, 146 : 941 - 946
  • [5] Application of 2-chloro-4,6-dimethoxy-1,3,5-triazine in the synthesis of 2-azetidinones
    Shiraz, Arnoosh Khademi
    Zarei, Maaroof
    MONATSHEFTE FUR CHEMIE, 2015, 146 (06): : 941 - 946
  • [6] An improved procedure for the large scale preparation of 2-chloro-4,6-dimethoxy-1,3,5-triazine
    Cronin, JS
    Ginah, FO
    Murray, AR
    Copp, JD
    SYNTHETIC COMMUNICATIONS, 1996, 26 (18) : 3491 - 3494
  • [7] Cobalt-Catalyzed Arylation or Benzylation of 2-Chloro-4,6-dimethoxy-1,3,5-triazine
    Begouin, Jeanne Marie
    Claudel, Stephanie
    Gosmini, Corinne
    SYNLETT, 2009, (19) : 3192 - 3194
  • [8] 2-CHLORO-4,6-DIMETHOXY-1,3,5-TRIAZINE - A NEW COUPLING REAGENT FOR PEPTIDE-SYNTHESIS
    KAMINSKI, ZJ
    SYNTHESIS-STUTTGART, 1987, (10): : 917 - 920
  • [9] 2-Chloro-4,6-dimethoxy-1,3,5-triazine: A New Effective and Convenient Coupling Reagent for Cephalosporin Derivatives
    Lee, H.-W.
    Kang, T. W.
    Cha, K. H.
    Kim, E.-N.
    Synthetic Communications, 28 (08):
  • [10] 2-chloro-4,6-dimethoxy-1,3,5-triazine: A new effective and convenient coupling reagent for cephalosporin derivatives
    Lee, HW
    Kang, TW
    Cha, KH
    Kim, EN
    Choi, NH
    Kim, JW
    Hong, CI
    SYNTHETIC COMMUNICATIONS, 1998, 28 (08) : 1339 - 1349
12345