Synthesis and Properties of Ethyl 1-Aryl-5-methyl4-[1-(phenylhydrazinylidene)ethyl]-1H-pyrazole-3-carboxylates

被引：3
|
作者：
Potopnyk, M. A. [1 ]
Matiichuk, V. S. [1 ]
Obushak, M. D. [1 ]
机构：
[1] Ivan Franko Natl Univ Lviv, Ul Kyrylla & Mefodiya 6, UA-79005 Lvov, Ukraine
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 53卷 / 01期
关键词：
FISCHER INDOLE SYNTHESIS;
D O I：
10.1134/S1070428017010110
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ethyl 1-aryl-4-acetyl-5-methyl-1H-pyrazole-3-carboxylates reacted with phenylhydrazine to give the corresponding hydrazones, ethyl 1-aryl-5-methyl-4-[1-(phenylhydrazinylidene)ethyl]-1H-pyrazole-3-carboxylates, which were converted to ethyl 1'-aryl-4-formyl-5'-methyl-1-phenyl-1H,1'H-3,4'-bipyrazole-3'-carboxylates by treatment with the Vilsmeier-Haack reagent. No indole derivatives were formed from the same hydrazones under the Fischer reaction conditions, but cyclization to 2-aryl-3,4-dimethyl-6-phenyl-2,6-dihydro-7H- pyrazolo[3,4-d] pyridazin-7-ones was observed.
引用
收藏
页码：62 / 65
页数：4
相关论文
共 50 条
  • [21] A NEW SYNTHESIS OF 1-ARYL-5-CYANO-1H-PYRAZOLE-4-CARBOXYLIC ACID, ETHYL-ESTERS
    BECK, JR
    ACKMANN, SA
    STASZAK, MA
    WRIGHT, FL
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) : 955 - 958
  • [22] Ethyl 1-(4-chlorobenzyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxylate
    Ge, Yan Qing
    Zhang, Ji Mei
    Wang, Guang Liang
    Xu, Hao
    Shi, Bo
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1387 - U483
  • [23] Ethyl 5-amino-1-(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-ylcarbonyl)3-methyl-1H-pyrazole-4-carboxylate
    Li, JF
    Song, HB
    Zhu, YQ
    Yang, HZ
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O1756 - O1758
  • [24] Synthesis of some novel 1-aryl-1H-1,2,3-triazole-4-carboxamides and ethyl 1-aryl-5-(1,2,3-triazol-1-yl)-1H-pyrazole-4-carboxylates
    Avigliano, Marialuce
    De Francesco, Debora
    Brizzi, Antonella
    Paolino, Marco
    Corelli, Federico
    Mugnaini, Claudia
    [J]. ARKIVOC, 2023, : 1 - 11
  • [25] 1-{3-[1-(Hydroxyimino)ethyl]-4-methyl-1H- pyrazol-5-yl}ethanone
    Malinkin, Sergey
    Penkova, Larysa
    Pavlenko, Vadim A.
    Haukka, Matti
    Pavlova, Svetlana V.
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2634 - +
  • [26] Ethyl 1-(2-bromoethyl)-3-ferrocenyl-1H-pyrazole-5-carboxylate
    Xie, Yong-Sheng
    Dong, Wen-Liang
    Zheng, Liang-Wen
    Zhang, Jin-Hua
    Zhao, Bao-Xiang
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : M978 - M979
  • [27] Synthesis of ethyl 5-acetyl-1-R-4-aryl-6-hydroxy-6-methyl-2-oxopiperidine-3-carboxylates
    M. S. Sargsyan
    S. S. Hayotsyan
    A. Kh. Khachatryan
    A. E. Badasyan
    G. A. Panosyan
    S. G. Kon’kova
    [J]. Chemistry of Heterocyclic Compounds, 2013, 48 : 1805 - 1808
  • [28] Synthesis of ethyl 5-acetyl-1-R-4-aryl-6-hydroxy-6-methyl-2-oxopiperidine-3-carboxylates
    Sargsyan, M. S.
    Hayotsyan, S. S.
    Khachatryan, A. Kh.
    Badasyan, A. E.
    Panosyan, G. A.
    Kon'kova, S. G.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 48 (12) : 1805 - 1808
  • [29] Ethyl 5-amino-3-(4,6-dimethylpyrimidin-2-ylamino)-1-methyl-1H-pyrazole-4-carboxylate and ethyl 5-amino-3-(4,6-dimethylpyrimidin-2-ylamino)-1-(2-nitrophenylsulfonyl)-1H-pyrazole-4-carboxylate
    Wu, C
    Zhu, YQ
    Li, HB
    Li, JR
    Ren, XL
    Li, B
    Yang, HZ
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O281 - O283
  • [30] Ethyl 5-(3,5-dimethyl-1H-pyrazol-1-ylsulfonyl)1-methyl-1H-pyrazole-4-carboxylate
    Zou, XM
    Shi, HL
    Yu, LM
    Yang, HZ
    Pei, J
    Liu, P
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O1812 - O1813
12345