A study of the reaction between 2,4-disubstituted-2,3-dihydro-1,5-benzothiazepines and ketenes generated in situ from chloro and dichloroacetyl chlorides

被引:3
|
作者
Xing, QY
Wang, HZ [1 ]
Zhou, X
Jin, S
Li, YM
Chan, ASC
机构
[1] Peking Univ, Sch Chem & Mol Engn, Beijing 100871, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1002/jhet.5570380302
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of triethyl amine, the reaction of 2,4-disubstituted-2,3-dihydro- 1,5-benzothiazepine with chloro and dichloroacetyl chlorides produced not only the expected beta -lactam derivative of the benzothiazepine, but also the ring opening product. Different results were obtained when the substituent at 2-position of the bexuothiazepine varied from methyl to aryl, and the substituent on the chloroacetyl chloride varied from H to Cl, or when carrying out the reaction at different temperatures. The structures of the obtained products and the reaction mechanism are discussed.
引用
收藏
页码:561 / 567
页数:7
相关论文
共 28 条
  • [1] Syntheses of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines
    Katritzky, AR
    Rogovoy, BV
    Chassaing, C
    Vvedensky, V
    Forood, B
    Flatt, B
    Nakai, H
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (06) : 1655 - 1658
  • [2] SYNTHESES OF 1,5-BENZOTHIAZEPINES .4. SYNTHESIS OF 2,4-DIARYL-2,3-DIHYDRO-1,5-BENZOTHIAZEPINES
    PANT, UC
    GAUR, BS
    CHUGH, M
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1988, 27 (08): : 752 - 753
  • [3] SYNTHESIS OF 2,4-DIARYL-3-(ARYLSULFONYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPINES
    REDDY, DB
    SANKARAIAH, B
    REDDY, S
    REDDY, NS
    REDDY, PVR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1993, 32 (11): : 1165 - 1167
  • [4] Synthesis of some new 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines and 2-aryl-4-(2′-hydroxy-3′/5′-chloro-5′/3′-hydroxymethylphenyl)-2,3-dihydro-1,5-benzothiazepines
    Gurav, VM
    Agarkar, SV
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1998, 37 (02): : 161 - 162
  • [5] Synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines as antibacterial and antifungal agents
    Barot, VM
    Patel, MR
    Naik, HB
    ASIAN JOURNAL OF CHEMISTRY, 2001, 13 (01) : 347 - 349
  • [6] Synthesis of 2,4-diaryl-1,5-benzodiazepines and 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines
    Padwad, M
    Ingle, VN
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1999, 76 (03) : 161 - 162
  • [7] Synthesis and steric structure of β-lactam derivatives of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines
    Xing, QY
    Li, Y
    Du, CY
    Yang, QQ
    Sun, N
    Jin, S
    CHINESE CHEMICAL LETTERS, 1998, 9 (10) : 919 - 921
  • [8] Synthesis and Steric Structure of β-Lactam Derivatives of 2,4-Diaryl-2,3-dihydro-1,5-benzothiazepines
    Qi Yi XING
    Yuan LI
    Cat Yun DU
    Qiu Qing YANGNa SUN
    ChineseChemicalLetters, 1998, (10) : 919 - 921
  • [9] NEW HETEROCYCLIC SYSTEM SYNTHESIS H THE REACTION OF 2,3-DIHYDRO-1,5-BENZOTHIAZEPINES WITH DICHLOROCARBENE
    Ruo Xi LAN Sheng JIN Department of Chemistry
    Chinese Chemical Letters, 1992, (01) : 9 - 10
  • [10] Catalyst-free synthesis of 2,3-dihydro-1,5-benzothiazepines in a renewable and biodegradable reaction medium
    Yadav, Neetu
    Yadav, Vijay B.
    Ansari, Mohd Danish
    Sagir, Hozeyfa
    Verma, Ankit
    Siddiqui, I. R.
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (18) : 7011 - 7014