Synthesis of 2,3-dihydro-1 3-thiazin-4(1H)ones and their remarkably facile recyclization to 2,3-dihydropyrimidin-4(1H)-ones

被引：14
|
作者：
Vovk, MV [1 ]
Sukach, VA [1 ]
Chernega, AN [1 ]
Pyrozhenko, VV [1 ]
Bol'but, AV [1 ]
Pinchuk, AM [1 ]
机构：
[1] Natl Acad Sci Ukraine, Inst Organ Chem, Kiev, Ukraine
来源：
HETEROATOM CHEMISTRY | 2005年 / 16卷 / 05期
关键词：
D O I：
10.1002/hc.20129
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Functionalized2,3-dihydro-1,3-thiazin-4 (1 H)-one derivatives have been synthesized by cyclo-condensation of 3-alkyl(aryl)amino-2-cyano-3-mercaptoacrylamides with aldehydes and ketones under acidic catalysis. 6-Alkyl(aryl)amino-5-cyano-2,3-dihydro- 1, 3-thiazin-4 (1H)-ones, when treated with a dilute solution of potassium hydroxide, are converted into the potassium salts of isomeric compounds, 1-alkyl(aryl)-5-cyano-6-mercapto-2,3-dihydropyrimidin-4(1H)-ones. Alkylation of the latter with dimethyl sulfate in situ furnishes 1-alkyl(aryl)-6-alkylthio-5cyano-2,3-dihydropyrimidin-4(1H)-ones, whereas boiling them in ethanol with an excess of hydrochloric acid leads to starting 2,3-dihydro-1,3-thiazin-4(1H)ones. (c) 2005 Wiley Periodicals, Inc.
引用
收藏
页码：426 / 436
页数：11
相关论文
共 50 条
  • [41] SYNTHESES OF 2,3-DIHYDRO-4(1H)-PYRIDONES
    SUGIYAMA, N
    YAMAMOTO, M
    KASHIMA, C
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (03) : 901 - +
  • [42] 2,3-DIHYDRO-4(1H)-QUINAZOLINONE DERIVATIVES
    BONOLA, G
    SIANESI, E
    JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (02) : 329 - &
  • [43] Synthesis of 2,3-Dihydro-4(1H)-quinolones and the Corresponding 4(1H)-Quinolones via Low-Temperature Fries Rearrangement of N-Arylazetidin-2-ones
    Lange, Jens
    Bissember, Alex C.
    Banwell, Martin G.
    Cade, Ian A.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2011, 64 (04) : 454 - 470
  • [44] Synthesis and Acylation of 4-Chloroalkyl-3,4-dihydropyrimidin-2(1H)-ones
    Kolosov, Maksim A.
    Kulyk, Olesia G.
    Al-Ogaili, Muataz
    Orlov, Valeriy D.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2012, 67 (09): : 921 - 924
  • [45] Microwave Irradiation Assisted Selective Synthesis of 4,6-Diaryl-3,4-dihydropyrimidin-2(1H)-ones and Pyrimidin-2(1H)-ones
    An, Lin
    Zhang, Ling
    Zheng, Youguang
    Xue, Yunsheng
    Mou, Jie
    Liu, Ling
    Liu, Yi
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1108 - 1111
  • [46] Thermal recyclization of 1-amino-2,3-dihydro-2,3-pyrrolediones to 2,3-dihydro-1h-pyrazol-3-ones [2]
    Konyukhova, N.A.
    Krasnykh, O.P.
    Maslivets, A.N.
    Chemistry of Heterocyclic Compounds, 2001, Kluwer Academic/Plenum Publishers (37) : 777 - 778
  • [47] The combined role of heterogeneous catalysis and ultrasonic waves on the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones
    Safari, Javad
    Gandomi-Ravandi, Soheila
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 : S415 - S424
  • [48] SYNTHESIS OF 2,3-DIHYDRO-1H-PHENOTHIAZIN-4(10H)-ONES
    MIYANO, S
    ABE, N
    SUMOTO, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (18) : 760 - 760
  • [49] ONE-POT SYNTHESIS OF 2,3-DIHYDRO-2,3-DISUBSTITUTED BENZO[G]-QUINAZOLIN-4(1H)-ONES
    KUMAR, PR
    REDDY, MS
    SYNTHETIC COMMUNICATIONS, 1992, 22 (17) : 2499 - 2508
  • [50] Ionic Liquid Catalyzed Expeditious Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1H)-ones and 2-Aryl-2,3-dihydro-4H-chromen-4-ones under Microwave Irradiation
    Kumar, Dalip
    Patel, Gautam
    Kumar, Anil
    Roy, Ram K.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (04) : 791 - 795
12345