THE PREPARATION OF KETENE DITHIOACETALS AND THIOPHENES FROM CHLOROPYRIDINES CONTAINING AN ACTIVE METHYLENE GROUP

被引:3
|
作者
Sturrock, Keith R. [1 ]
Bremner, David H. [1 ]
Wishart, Grant [2 ]
机构
[1] Univ Abertay Dundee, Sch Contemporary Sci, Dundee DD1 1HG, Scotland
[2] Schering Plough Res Inst, Dept Chem, Newhouse ML1 5SH, Lanark, Scotland
关键词
Base Catalysed Reaction; Cyclization; Thorpe Reaction; Dieckmann Reaction; Carbon Disulfide; HALOGENATED PYRIDINE-DERIVATIVES; THIENOPYRIDINES; KETENDERIVATE;
D O I
10.3987/COM-10-S(E)59
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The base catalysed reaction of carbon disulphide with the active methylene groups of chloropyridines 4 and 7, followed by alkylation with reagents which also contain active methylene groups, lead to ketene dithioacetals. Further reaction with base afforded highly substituted thiophenes.
引用
收藏
页码:1657 / +
页数:7
相关论文
共 50 条
  • [21] REACTIONS OF BETA-DICARBONYL COMPOUNDS, CONTAINING A ACTIVE METHINE OR METHYLENE GROUP, WITH DIAZONIUM SALTS
    POMAZANSKAKOLODZIEJSKA, T
    ACTA POLONIAE PHARMACEUTICA, 1975, 32 (03): : 393 - 395
  • [22] PREPARATION OF PROTECTED BETA-KETO ALDEHYDES FROM BETA-KETO-ESTERS VIA SELECTIVE REDUCTION OF ACYL(ALKOXYCARBONYL)KETENE DITHIOACETALS
    CHOI, EB
    YOUN, IK
    PAK, CS
    SYNTHESIS-STUTTGART, 1988, (10): : 792 - 794
  • [23] PHOSPHONATE ESTER PREPARATION FROM ACTIVE METHYLENE-COMPOUNDS AND PHOSPHOROCHLORIDATE ESTERS
    COMINS, DL
    JACOBINE, AF
    MARSHALL, JL
    TURNBULL, MM
    SYNTHESIS-STUTTGART, 1978, (04): : 309 - 311
  • [24] STUDIES ON UNSATURATED LACTONES .27. INTERACTION OF COMPOUNDS CONTAINING ACTIVE METHYLENE GROUP AND ALPHA-KETOLS
    AVETISYAN, AA
    DZHANDZHAPANYAN, AN
    BAYATYAN, BE
    DANGYAN, MT
    ARMYANSKII KHIMICHESKII ZHURNAL, 1975, 28 (10): : 819 - 823
  • [25] STUDY OF THIOSULFONIC ACIDS .32. REACTION OF ARYL ESTERS OF THIOSULFONIC ACIDS WITH SUBSTANCES, CONTAINING AN ACTIVE METHYLENE GROUP
    BOLDYREV, BG
    ARISTARKHOVA, LN
    STOYANOVSKAYA, YI
    BILOZOR, TK
    ZHURNAL ORGANICHESKOI KHIMII, 1984, 20 (06): : 1276 - 1283
  • [26] Receptor with an Active Methylene Group as Binding Site for Extraction of Inorganic Fluoride Ions from Seawater
    Madhuprasad
    Trivedi, Darshak R.
    CHEMPLUSCHEM, 2014, 79 (07): : 1001 - 1008
  • [27] Preparation ofMT-type polysiloxane containing active vinyl groups with low hydroxyl group content
    Guo, Shiping
    Liu, Qingyue
    Dong, Hong
    Qu, Zhirong
    Wu, Chuan
    JOURNAL OF APPLIED POLYMER SCIENCE, 2021, 138 (07)
  • [28] SYNTHESIS AND INVESTIGATION OF PHYSIOLOGICALLY ACTIVE PHOSPHORIC-ACID ETHERS CONTAINING TRICHLOROMETHYL GROUP - PREPARATION CHLOPHOSPHOL
    SHEPELEVA, ES
    SANIN, PI
    TARAKHOV.ML
    TIMOSHEN.YG
    BORODACH, MS
    GELFER, AP
    KIM, OT
    KAGAN, YS
    FERFILFA.IL
    DOKLADY AKADEMII NAUK SSSR, 1972, 203 (04): : 856 - +
  • [29] Spectrofluorimetric determination of drugs containing active methylene group using N1-methyl nicotinamide chloride as a fluorigenic agent
    El Dawy, Mohamed Abdelfattah
    Mabrouk, Mokhtar Mohamed
    El Barbary, Riad Ahmed
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (07) : 1026 - 1029
  • [30] Stereoselective Knoevenagel reaction between pyrimidine carbaldehyde bearing an adjacent aryl group and active cyano-containing methylene compounds
    Yoshikawa, Takahiro
    Hayashi, Naoto
    Yamada, Akihiro
    Yokota, Masayuki
    TETRAHEDRON LETTERS, 2023, 116