Synthesis of 2-Aryl-5-oxo-4-[2-(phenylmethylidene)hydrazino]-2,5-dihydro-1H-pyrrole-3-carboxylates by the Reaction between Hydrazones, Acetylenedicarboxylates, and 1-Aryl-N,N′-bis(arylmethylidene)methanediamines

被引:1
作者
Alizadeh, Abdolali [1 ]
Saberi, Vahid [1 ]
Mokhtari, Javad [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
关键词
Hydrazine hydrate; Aldehydes; Acetylenedicarboxylates; dialkyl; Methanediamine; 1-aryl-N; N-bis(arylmethylidene)-; Multicomponent reactions;
D O I
10.1002/hlca.201300116
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient approach for the preparation of functionalized 2-aryl-2,5-dihydro-5-oxo-4-[2-(phenylmethylidene)hydrazino]-1H-pyrroles is described. The four-component reaction between aldehydes, NH2NH2H2O, dialkyl acetylenedicarboxylates, and 1-aryl-N,N-bis(arylmethylidene)methanediamines proceeds in EtOH under reflux in good-to-excellent yields (Scheme1). The structures of 4 were corroborated spectroscopically (IR, H-1- and C-13-NMR, and EI-MS, and, in the case of 4f, by X-ray crystallography). A plausible mechanism for this type of reaction is proposed (Scheme2).
引用
收藏
页码:1991 / 1996
页数:6
相关论文
共 9 条
  • [1] Synthesis of Heterocyclic [3.3.3]Propellanes via a Sequential Four-Component Reaction
    Alizadeh, Abdolali
    Rezvanian, Atieh
    Zhu, Long-Guan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09) : 4385 - 4390
  • [2] CATALYST-FREE SYNTHESIS OF α-AMINOACYL-AMIDES VIA N,N′-BIS(PHENYLMETHYLIDENE)PHENYLMETHANEDIAMINE AS IMINE SURROGATE IN UGI MULTICOMPONENT REACTION
    Alizadeh, Abdolali
    Mokhtari, Javad
    [J]. SYNTHETIC COMMUNICATIONS, 2012, 42 (05) : 686 - 693
  • [3] Efficient 3D database screening for novel HIV-1IN inhibitors
    Barreca, ML
    Rao, A
    De Luca, L
    Zappalà, M
    Gurnari, C
    Monforte, P
    De Clercq, E
    Van Maele, B
    Debyser, Z
    Witvrouw, M
    Briggs, JM
    Chimirri, A
    [J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 2004, 44 (04): : 1450 - 1455
  • [4] Synthesis of functionalized pyrroles and 6,7-dihydro-1H-indol-4(5H)-ones by reaction of 1,3-dicarbonyl compounds with 2-azido-1,1-diethoxyethane
    Bellur, E
    Langer, P
    [J]. TETRAHEDRON LETTERS, 2006, 47 (13) : 2151 - 2154
  • [5] Dömling A, 2005, MULTICOMPONENT REACTIONS, P76, DOI 10.1002/3527605118.ch3
  • [6] Studies on the Reaction of Diimines with Thiourea: Synthesis and Solvent-Induced cis/trans-Isomerization of 1,3,5-Triazinane-2-thiones
    Kaboudin, Babak
    Ghasemi, Tahereh
    Yokomatsu, Tsutomu
    [J]. SYNTHESIS-STUTTGART, 2009, (18): : 3089 - 3093
  • [7] Synthesis and antimicrobial activity of some new hydrazones of 4-fluorobenzoic acid hydrazide and 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines
    Rollas, S
    Gulerman, N
    Erdeniz, H
    [J]. FARMACO, 2002, 57 (02): : 171 - 174
  • [8] Arming antibodies: prospects and challenges for immunoconjugates
    Wu, AM
    Senter, PD
    [J]. NATURE BIOTECHNOLOGY, 2005, 23 (09) : 1137 - 1146
  • [9] Practical synthesis and mechanistic study of polysubstituted tetrahydropyrimidines with use of domino multicomponent reactions
    Zhu, Qiuhua
    Jiang, Huanfeng
    Li, Jinghao
    Zhang, Min
    Wang, Xiujun
    Qi, Chaorong
    [J]. TETRAHEDRON, 2009, 65 (23) : 4604 - 4613