A Novel, Fast and Efficient One-Pot Four-Component Procedure for Preparation of Some Alkyl Spiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizine]-2′-carboxylates

被引:14
|
作者
Karsalary, A. Alizadeh [2 ]
Mohammadizadeh, M. R. [1 ]
Hasaninejad, A. R. [1 ]
Mohammadi, A. A. [3 ]
Karimi, A. R. [4 ]
机构
[1] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr 75169, Iran
[2] Islamic Azad Univ, Savad Kooh Branch, Dept Chem, Savad Kooh, Iran
[3] Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran, Iran
[4] Arak Univ, Dept Chem, Arak 38156, Iran
关键词
Ninhydrin; Phenylenediamines; Proline; Alkyl acrylates; Alkyl spiro[indeno[1,2-b]quinoxaline-11,3 '-pyrrolizine]-2 '-carboxylates; 1,3-DIPOLAR CYCLOADDITION REACTIONS; ALPHA-AMINO-ACIDS; X=Y-ZH SYSTEMS; MULTICOMPONENT REACTIONS; AZOMETHINE YLIDES; PYRROLIZIDINE ALKALOIDS; DECARBOXYLATIVE ROUTE; POTENTIAL 1,3-DIPOLES; METHODOLOGY; DERIVATIVES;
D O I
10.1007/BF03245858
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study we report a novel one-pot reaction which stereoselectively affords alkyl spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylates via the four-component condensation of ninhydrin, phenylenediamines, proline, and acrylic acid derivatives. The reactions were run in ethanol and completed at less than 25 min and the products were obtained in very good yields. The stereochemistry of the products was deduced on the basis of the H-1 NOESY and comparison with the related systems.
引用
收藏
页码:45 / 50
页数:6
相关论文
共 50 条
  • [41] A one-pot four-component synthesis of N-arylidene-2-aryl-imidazo[1,2-a]azin-3-amines
    Rahmati, Abbas
    Moazzam, Ali
    Khalesi, Zahra
    TETRAHEDRON LETTERS, 2014, 55 (29) : 3840 - 3843
  • [42] Ethyl 1 ''-benzyl-2 ''-oxo-2 ',3 ',5 ',6 ',7 ',7a '-hexahydro-1 ' H-dispiro[indeno[1,2-b]quinoxaline-11,2 '-pyrrolizine-3 ',3 '' indoline]-1 '-carboxylate monohydrate
    Kannan, Piskala Subburaman
    Lanka, Srinu
    Thennarasu, Sathiah
    Vimala, Gopal
    SubbiahPandi, Arunachalathevar
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O854 - +
  • [43] Synthesis of 1'-aryl-3''-(1H-benzotriazol-1-yl)-5',5'',6',6'',7',7a'-hexahydro-1'H,8''H-dispiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine-2',7''-indolizin]-8''-ones via cycloaddition reaction
    Yulin Ling
    Yulin Huang
    Xiaofang Li
    Chemistry of Heterocyclic Compounds, 2021, 57 : 181 - 186
  • [44] Synthesis of 1′-aryl-3"-(1H-benzotriazol-1-yl)-5′,5",6′,6",7′,7a′-hexahydro-1′H,8"H-dispiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizine-2′,7"-indolizin]-8"-ones via cycloaddition reaction
    Ling, Yulin
    Huang, Yulin
    Li, Xiaofang
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (02) : 181 - 186
  • [45] One-pot, three-component synthesis of spiro[indeno[1,2-b]quinoline-10,3′-pyrroles] via the Hantzsch-type reaction of 1H-pyrrole-2,3-diones
    Dmitriev, Maksim V.
    Salnikova, Tatyana V.
    Silaichev, Pavel S.
    Maslivets, Andrey N.
    TETRAHEDRON LETTERS, 2017, 58 (01) : 67 - 70
  • [46] Silica sodium carbonate: the most efficient catalyst for the one-pot synthesis of indeno[1,2-b]quinoline and spiro[chromene-4,3′-indoline]-3-carbonitriles under solvent-free condition
    Vijay V. Shinde
    Mudumala Veeranarayana Reddy
    Yong Hyun Kim
    Byung Kwon Cho
    Yeon Tae Jeong
    Monatshefte für Chemie - Chemical Monthly, 2015, 146 : 673 - 682
  • [47] Silica sodium carbonate: the most efficient catalyst for the one-pot synthesis of indeno[1,2-b]quinoline and spiro[chromene-4,3'-indoline]-3-carbonitriles under solvent-free condition
    Shinde, Vijay V.
    Reddy, Mudumala Veeranarayana
    Kim, Yong Hyun
    Cho, Byung Kwon
    Jeong, Yeon Tae
    MONATSHEFTE FUR CHEMIE, 2015, 146 (04): : 673 - 682
  • [48] Efficient and extremely facile one-pot four-component synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by p-TsOH•H2O
    Sajadikhah, Seyed Sajad
    Maghsoodlou, Malek Taher
    Hazeri, Nourallah
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (04) : 2503 - 2511
  • [49] Crystal structure of 1 ',1 ''-dimethyl-4 '-(4-cholorophenyl)dispiro[11H-indeno[1,2-b]quinoxaline-11,2 '-pyrrolidine-3 ',3 ''-piperidin]-4 ''-one
    Nagalakshmi, R. A.
    Suresh, J.
    Malathi, K.
    Kumar, R. Ranjith
    Lakshman, P. L. Nilantha
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O68 - U258
  • [50] Efficient and extremely facile one-pot four-component synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by p-TsOH·H2O
    Seyed Sajad Sajadikhah
    Malek Taher Maghsoodlou
    Nourallah Hazeri
    Research on Chemical Intermediates, 2015, 41 : 2503 - 2511