1,3-DIPOLAR CYCLOADDITION OF 5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLIUM BETAINES

被引：12
|
作者：
KIM, DJ [1 ]
YOO, KH [1 ]
PARK, SW [1 ]
机构：
[1] KOREA ADV INST SCI & TECHNOL,DIV CHEM,SEOUL 131650,SOUTH KOREA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 08期
关键词：
D O I：
10.1021/jo00034a029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
5,6-Dihydroimidazo[2,1-b]thiazolium betaines were generated in situ from 3,7-disubstituted 5,6-dihydroimidazo[2,1-b]thiazolium bromides and triethylamine. The reaction of these imidazothiazolium betaines with acetylenic dipolarophiles, such as ethyl propiolate, dimethyl acetylenedicarboxylate, and dibenzoylacetylene, provided geometric cis,trans isomers containing 2,3-dihydro-1H-pyrrolo[1,2-a]imidazole. We have proposed a mechanism of this reaction that involves 1,3-dipolar cycloaddition, isomeric rearrangement, and then nucleophilic addition successively. The ratio of trans and cis isomers depended on the temperature and solvents. The stereoselectivity of trans isomers increased with increasing temperature and decreasing polarity of solvents.
引用
收藏
页码：2347 / 2352
页数：6
相关论文
共 50 条
  • [1] A 5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLE DERIVATIVE
    ZUKERMANSCHPECTOR, J
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1994, 50 : 2077 - 2079
  • [2] Synthesis of quaternary 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazolium salts
    Dianov, V. M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (07) : 1028 - 1030
  • [3] Synthesis of quaternary 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazolium salts
    V. M. Dianov
    Russian Journal of Organic Chemistry, 2006, 42 : 1028 - 1030
  • [4] Inhibiting action of 1,2-diaryl-5,6-dihydroimidazo[2,1-b]-thiazolium bromides on acid corrosion of steel
    Sizaya, OI
    Kosukhina, LD
    Chumakov, VA
    Demchenko, AM
    Krasovskii, AN
    RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 1996, 69 (09) : 1342 - 1345
  • [5] Inhibiting action of 1,2-diaryl-5,6-dihydroimidazo[2,1-b]-thiazolium bromides on acid corrosion of steel
    Chernigov Technological Institute, Chernigov, Ukraine
    Russ. J. Appl. Chem., 9 (1342-1345):
  • [6] Identification of 5,6-dihydroimidazo[2,1-b]thiazoles as a new class of antimicrobial agents
    Li, Yangmei
    Bionda, Nina
    Fleeman, Renee
    Wang, Hongjie
    Ozawa, Akihiko
    Houghten, Richard A.
    Shaw, Lindsey
    BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (21) : 5633 - 5638
  • [7] 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 - &
  • [8] DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL THIIRANES BY 1,3-DIPOLAR CYCLOADDITION OF IMIDAZO[2,1-B]THIAZOLIUM-4-OLATE SYSTEMS WITH AROMATIC-ALDEHYDES
    ARECES, P
    AVALOS, M
    BABIANO, R
    GONZALEZ, L
    JIMENEZ, JL
    MENDEZ, MM
    PALACIOS, JC
    TETRAHEDRON LETTERS, 1993, 34 (18) : 2999 - 3002
  • [9] BSA binding and antibacterial studies of newly synthesized 5,6-Dihydroimidazo[2,1-b]thiazole-2-carbaldehyde
    Yallur, Basappa Chanabasappa
    Katrahalli, Umesha
    Krishna, Panchangam Murali
    Hadagali, Manjunatha Devagondanahalli
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2019, 222
  • [10] Pyrrolo[2,1-b]thiazole Derivatives by Asymmetric 1,3-Dipolar Reactions of Thiazolium Azomethine Ylides to Activated Vinyl Sulfoxides
    Garcia Ruano, Jose Luis
    Fraile, Alberto
    Rosario Martin, M.
    Gonzalez, Gema
    Fajardo, Cristina
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) : 8484 - 8490
12345