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
  • [21] Synthesis and Evaluation of Antimicrobial and Anti-inflammatory Activity of 6-aryliden-2-methyl-2,3-dihydroimidazo[2,1-b][1,3]thiazoles
    Saliyeva, Lesya
    Holota, Serhii
    Grozav, Alina
    Yakovychuk, Nina
    Litvinchuk, Mariia
    Slyvka, Nataliia
    Vovk, Mykhailo
    BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2022, 12 (01): : 292 - 303
  • [22] Unexpected aminolysis reaction of 2-methyl-2,3-dihydroimidazo[2,1-b][1,3]thiazol-5(6H)-one
    Saliyeva, Lesya N.
    Slyvka, Nataliia Yu.
    Vas'kevich, Ruslan I.
    Rusanov, Eduard B.
    Vovk, Mykhailo V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (09) : 902 - 904
  • [23] DERIVATIVES OF IMIDAZO[2,1-B]THIAZOLE .9. REACTIONS OF 3-PHENACYL-5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLE AND 3-PHENACYLIDENE-2,3,5,6-TETRAHYDROIMIDAZO[2,1-B]THIAZOLE WITH HYDROXYLAMINE HYDROCHLORIDE
    HABLOUJ, M
    ROBERT, JF
    VEBREL, J
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (04) : 1105 - 1108
  • [24] 6-Nitro-2,3-dihydroimidazo[2,1-b][1,3]thiazoles: Facile synthesis and comparative appraisal against tuberculosis and neglected tropical diseases
    Thompson, Andrew M.
    Blaser, Adrian
    Palmer, Brian D.
    Anderson, Robert F.
    Shinde, Sujata S.
    Launay, Delphine
    Chatelain, Eric
    Maes, Louis
    Franzblau, Scott G.
    Wan, Baojie
    Wang, Yuehong
    Ma, Zhenkun
    Denny, William A.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (11) : 2583 - 2589
  • [25] 2-(4-Fluorophenyl)-N-{4-[6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazol-5-yl]pyridin-2-yl}acetamide
    Selig, Roland
    Schollmeyer, Dieter
    Albrecht, Wolfgang
    Laufer, Stefan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1132 - U601
  • [26] Synthesis of novel 2,3-dihydroimidazo[2,1-b][1,3]oxazoles through intramolecular nucleophilic ipso-substitution in 2-alkylsulfonylimidazoles
    Moreno, P
    Heras, M
    Maestro, M
    Villalgordo, JM
    SYNTHESIS-STUTTGART, 2002, (18): : 2691 - 2700
  • [27] 6-METHYL-5-THIOFORMYLPYRROLO[2,1-B]THIAZOLE
    KILLEAN, RCG
    LAWRENCE, JL
    CAMERON, JU
    SHARMA, A
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1975, 31 (APR15): : 1217 - 1219
  • [28] THE ANTI-INFLAMMATORY ACTIVITY OF 2,3-DIHYDROIMIDAZO[2,1-B]THIAZOLES - STUDY OF THE ISOMERIC 5/6-(4-PYRIDYL) AND 6/5-(4-SUBSTITUTEDPHENYL) COMPOUNDS
    LANTOS, I
    BENDER, P
    RAZGAITIS, C
    SUTTON, BM
    DIMARTINO, M
    GRISWOLD, D
    WALZ, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 60 - MEDI
  • [29] PROTONATION OF IMIDAZO[2,1-B]THIAZOLE AND THIAZOLO[2,3-F]PURINE
    ALEKSEEVA, LM
    DVORYANT.GG
    SHEINKER, YN
    MAZUR, IA
    KURMAZ, BV
    KOCHERGI.PM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1974, (09): : 1206 - 1211
  • [30] 5-SUBSTITUTED 6-AMINO-2,3-DIHYDROIMIDAZO[2,1-B]THIAZOLES AND 2-AMINO-5,6-DIHYDROTHIAZOLO[3,2-B]-1,2,4-TRIAZOLE
    IWATA, C
    WATANABE, M
    OKAMOTO, S
    FUJIMOTO, M
    SAKAE, M
    KATSURADA, M
    IMANISHI, T
    SYNTHESIS-STUTTGART, 1988, (03): : 261 - 262
12345