HETEROARYLATION OF 6-ARYL-2,3-DIHYDROIMIDAZO[2,1-B]THIAZOLE WITH N-(ETHOXYCARBONYL)HETEROAROMATIC SALTS

被引：3
|
作者：
SHILCRAT, S
LANTOS, I
MCGUIRE, M
PRIDGEN, L
DAVIS, L
EGGLESTON, D
STAIGER, D
WEBB, L
机构：
[1] Division of Chemical Research & Development, Smith Kline & French Laboratories, King of Prussia, Pennsylvania, 19406-0939
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1993年 / 30卷 / 06期
关键词：
D O I：
10.1002/jhet.5570300634
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The ethyl chloroformate salts of a variety of benzo-fused six membered pi-deficient heteroaromatics, including quinoline, isoquinoline, 4-chloroquinoline, 3-bromoquinoline, phthalazine, and quinazoline, reacted with 6-aryl-2,3-dihydroimidazo[2,1-b]thiazole at the 5-position. The dihydroheteroaromatic adducts were oxidized by o-chloranil, sulfur, or electrochemical methodology to form the 5-heteroaromatic-6-aryl-2,3-dihydroimidazo[2,1-b]thiazoles, 10-15. In each example, the regiochemistry of addition to the heteroaromatic ring was established.
引用
收藏
页码：1663 / 1671
页数：9
相关论文
共 50 条
  • [31] Efficient Access to Original 6-Substituted 5-Nitro-2,3-dihydroimidazo-[2,1-b]oxazoles
    Mathias, Fanny
    Kabri, Youssef
    Crozet, Maxime D.
    Vanelle, Patrice
    SYNTHESIS-STUTTGART, 2017, 49 (12): : 2775 - 2785
  • [32] PHENACYLTHIOIMIDAZOLINES AND 3-ARYL-5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLES WITH ANTIDEPRESSANT ACTIVITY
    SHARPE, CJ
    SHADBOLT, RS
    ASHFORD, A
    ROSS, JW
    JOURNAL OF MEDICINAL CHEMISTRY, 1971, 14 (10) : 977 - &
  • [33] NEW SYNTHESIS OF 6-ACETYLIMIDAZO[2,1-B]THIAZOLE DERIVATIVES
    SPRIO, V
    MIGLIARA, O
    AJELLO, E
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (01) : 91 - 92
  • [34] STRUCTURAL MODIFICATION OF 5-ARYL-2,3-DIHYDROIMIDAZO[2,1-A]ISOQUINOLINE PLATELET-ACTIVATING-FACTOR RECEPTOR ANTAGONISTS
    HOULIHAN, WJ
    CHEON, SH
    PARRINO, VA
    HANDLEY, DA
    LARSON, DA
    JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (21) : 3098 - 3102
  • [35] High throughput synthesis of 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b]thiazole derivatives
    Li, Yangmei
    Giulianotti, Marc
    Houghten, Richard A.
    TETRAHEDRON LETTERS, 2011, 52 (06) : 696 - 698
  • [36] IMMUNOMODULATORY ACTIVITY OF THE NEWLY SYNTHESIZED COMPOUND TOK-8801 (N-(2-PHENYLETHYL)-3,6,6-TRIMETHYL-5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLE-2-CARBOXAMIDE)
    FUJIWARA, M
    SHIBATA, K
    TAKAYANAGI, N
    MATSUNARI, K
    YAMAMOTO, I
    JAPANESE JOURNAL OF PHARMACOLOGY, 1989, 51 (04): : 549 - 554
  • [37] ANTIINFLAMMATORY ACTIVITY OF 5,6-DIARYL-2,3-DIHYDROIMIDAZO[2,1-B]THIAZOLES - ISOMERIC 4-PYRIDYL AND 4-SUBSTITUTED PHENYL DERIVATIVES
    LANTOS, I
    BENDER, PE
    RAZGAITIS, KA
    SUTTON, BM
    DIMARTINO, MJ
    GRISWOLD, DE
    WALZ, DT
    JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (01) : 72 - 75
  • [38] A new class of fused imidazoles by intramolecular nucleophilic ipso-substitution in 2-alkylsulfonylimidazoles:: Synthesis of 2,3-dihydroimidazo[2,1-b][1,3]oxazoles
    Heras, M
    Ventura, M
    Linden, A
    Villalgordo, JM
    SYNTHESIS-STUTTGART, 1999, (09): : 1613 - 1624
  • [39] IMIDAZO(2,1-B)THIAZOLE DERIVATIVES .7. FUNGISTATIC ACTIVITIES OF 3-AROYLMETHYL AND 3-(BETA-ARYL BETA-HYDROXY)-ETHYL-5,6-DIHYDROIMIDAZO(2,1-B)THIAZOLES
    HABLOUJ, M
    ROBERT, JF
    PANOUSE, JJ
    SIMERAY, J
    CHAUMONT, JP
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1986, 21 (06) : 499 - 504
  • [40] STRUCTURE OF 6-(4-CHLOROBENZYLIDENE)-2,3-DIHYDROIMIDAZO[2,1-B]THIAZOL-5(6H)-ONE CONFORMATIONAL-ANALYSIS OF Z ISOMERS OF 5-BENZYLIDENETHIOHYDANTOIN DERIVATIVES
    KAROLAKWOJCIECHOWSKA, J
    KIECKONONOWICZ, K
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 : 2371 - 2374
12345