Efficient catalyst-free tricomponent synthesis of new spiro[cyclohexane-1,4′-pyrazolo[3,4-e][1,4]thiazepin]-7′(6′H)-ones

被引:5
|
作者
Becerra-Rivas, Christian [1 ]
Cuervo-Prado, Paola [1 ]
Orozco-Lopez, Fabian [1 ]
机构
[1] Univ Nacl Colombia, Grp Studies Synth & Applicat Heterocycl Cpds, Ciudad Univ, Bogota 14490, Colombia
关键词
Spiroheterocycles; 1,4-thiazepin-3-ones; aminopyrazoles; tricomponent reaction; catalyst-free; DERIVATIVES; DISCOVERY; SERIES;
D O I
10.1080/00397911.2018.1554143
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of spirocyclohexane-1,4 '-pyrazolothiazepinones were synthesized by one-pot multicomponent cyclocondensation reactions between 5-amino-1-arylpyrazoles, cyclohexanone and mercaptoacetic acid with good yields and easy purification protocols. Some control experiments involving isolation of reaction intermediates were performed leading to the proposal of three alternative mechanistic pathways conducting to the named spiroheterocycles. All target molecules were fully characterized by IR, NMR, melting point and HRMS. [GRAPHICS] .
引用
收藏
页码:367 / 376
页数:10
相关论文
共 50 条
  • [31] SYNTHESIS OF 4-(O-FLUOROPHENYL)-6,8-DIHYDRO-3,8-DIMETHYL-PYRAZOLO [3,4-E] [1,4] DIAZEPIN-7(1H)ONE, A METABOLITE OF ZOLAZEPAM
    DEWALD, HA
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (06) : 1061 - 1062
  • [32] 3,7-DIHYDRO-5-PHENYLPYRROLO [3,4-E] [1,4]-DIAZEPIN-2(1H)-ONES SYNTHESIS AND PHARMACOLOGICAL PROPERTIES
    FONTANELLA, L
    MARIANI, L
    TARZIA, G
    CORSICO, N
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1976, 11 (03) : 217 - 220
  • [33] Synthesis of spirocyclic 4,5,5a,6,7,8-hexahydro-1H-pyrazolo[3,4-e]indolizine derivatives
    Eltsov, OS
    D'yachenko, EV
    Glukhareva, TV
    Morzherin, YY
    MENDELEEV COMMUNICATIONS, 2005, 15 (03) : 119 - 120
  • [34] HETEROCYCLIC-SYSTEMS .5. SYNTHESIS OF 1H,4H,6H-PYRAZOLO[3,4-E]PYRROLO-[2,1-C][1,4]OXAZEPINE DERIVATIVES
    MASSA, S
    STEFANCICH, G
    ARTICO, M
    CORELLI, F
    ORTENZI, G
    HETEROCYCLES, 1985, 23 (06) : 1417 - 1423
  • [35] Synthesis and characterization of 4,5-dihydro-1H-pyrazolo[3,4b] [1,4]azaphosphinines
    Tolmachev, AA
    Dovgopoly, SI
    Kostyuk, AN
    Kozlov, ES
    Pushechnikov, AO
    Holzer, W
    HETEROATOM CHEMISTRY, 1999, 10 (05) : 391 - 398
  • [36] SYNTHESIS OF PYRAZOLO[3,4-E][1,4]-DIAZEPIN-4,7-DIONE DERIVATIVES HAVING ACTIVITY ON THE CENTRAL NERVOUS-SYSTEM
    SPRIO, V
    CARONNA, S
    MIGLIARA, O
    PETRUSO, S
    MATERA, M
    FARMACO, 1989, 44 (09): : 809 - 818
  • [37] Pyrazoles as building blocks in heterocyclic synthesis: Synthesis of pyrazolo [3,4-d]pyrimidine, pyrazolo[3,4-e][1,4]diazepine, pyrazolo [3,4-d][1,2,3]triazine and pyrolo [4,3-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives
    A. -F. A. Harb
    H. H. Abbas
    F. H. Mostafa
    Journal of the Iranian Chemical Society, 2005, 2 : 115 - 123
  • [38] Synthesis of 1′-substituted 4′,4′-dimethyl-6′-methoxy-4′H-spiro[cyclohexane-1,3′-isoquinolines]
    A. N. Perevoshchikova
    A. A. Gorbunov
    Yu. S. Rozhkova
    P. A. Slepukhin
    Yu. V. Shklyaev
    Russian Journal of Organic Chemistry, 2014, 50 : 513 - 517
  • [39] 10H-BENZ[B]PYRIDAZINO[3,4-E][1,4]THIAZIN UND 5H-BENZ[B]PYRIDAZINO[4,3-E][1,4]THIAZIN
    YONEDA, F
    OHTKAKA, T
    NITTA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1963, 11 (07) : 954 - +
  • [40] Synthesis of 1'-substituted 4',4'-dimethyl-6'-methoxy-4'H-spiro[cyclohexane-1,3'-isoquinolines]
    Perevoshchikova, A. N.
    Gorbunov, A. A.
    Rozhkova, Yu. S.
    Slepukhin, P. A.
    Shklyaev, Yu. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (04) : 513 - 517