Triethylammonium acetate-mediated domino-Knoevenagel-hetero-Diels-Alder reaction: synthesis of some angular polyheterocycles

被引:10
|
作者
Parmar, Narsidas J. [1 ]
Pansuriya, Bhavesh R. [1 ]
Barad, Hitesh A. [1 ]
Parmar, Bhagyashri D. [1 ]
Kant, Rajni [2 ]
Gupta, Vivek K. [2 ]
机构
[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India
[2] Univ Jammu, Postgrad Dept Phys, Jammu 180006, India
来源
MONATSHEFTE FUR CHEMIE | 2013年 / 144卷 / 06期
关键词
Angular polyheterocycles; Green chemistry; Ketones; Lewis acids; One-pot synthesis; Pericyclic reactions; DIASTEREOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; NATURAL-PRODUCTS; DERIVATIVES; TANDEM; ANNULATION; STRATEGIES; CHEMISTRY; SEQUENCE; CATALYST;
D O I
10.1007/s00706-012-0873-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A solvent-cum catalyst, ionic liquid triethylammonium acetate-mediated one-pot procedure for the synthesis of some new angular benzopyrano[3,4-c]pyrano-fused pyrazoles, all of which incorporate a tertiary ring junction carbon, has been developed. The stereochemistry of the products has been confirmed by single-crystal X-ray diffraction data.
引用
收藏
页码:865 / 878
页数:14
相关论文
共 45 条
  • [31] Synthesis of 1H,7H,12bH-Pyrano[3′,4′:5,6]pyrano[3,4-c][1]benzopyran-1-one via Domino Knoevenagel/Hetero-Diels?Alder Reaction with Theoretical Investigations
    Khoshkholgh, Malihe Javan
    Hosseindokht, Mohammad Reza
    Balalaie, Saeed
    Bozorgmehr, Mohammad Reza
    Bijanzadeh, Hamid Reza
    HELVETICA CHIMICA ACTA, 2012, 95 (01) : 52 - 60
  • [32] Efficient access to novel hexahydro-chromene and tetrahydro-pyrano[2,3-d]pyrimidine-annulated benzo-δ-sultones via a domino Knoevenagel-hetero-Diels-Alder reaction in water
    Ghandi, Mehdi
    Mohammadimehr, Elham
    Sadeghzadeh, Masoud
    Bozcheloei, Abolfazl Hasani
    TETRAHEDRON, 2011, 67 (44) : 8484 - 8491
  • [33] Efficient one-pot synthesis of benzopyranobenzopyrans and naphthopyranobenzopyrans by domino aldol-type reaction/hetero Diels-Alder reaction of resorcinols and naphthols
    Lee, Yong Rok
    Kim, Yun Mi
    Kim, Sung Hong
    TETRAHEDRON, 2009, 65 (01) : 101 - 108
  • [34] Catalyst-free regioselective synthesis of benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(4H)-one derivatives by domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes with 4-hydroxy dithiocoumarin in aqueous medium
    Majumdar, K. C.
    Taher, Abu
    Ponra, Sudipta
    TETRAHEDRON LETTERS, 2010, 51 (17) : 2297 - 2300
  • [35] ZnBr2 catalyzed domino Knoevenagel-hetero-Diels-Alder reaction: An efficient route to polycyclic thiopyranoindol annulated [3,4-c] quinolone derivatives
    Kiamehr, Mostafa
    Alipour, Batoul
    Mohammadkhani, Leyla
    Jafari, Behzad
    Langer, Peter
    TETRAHEDRON, 2017, 73 (21) : 3040 - 3047
  • [36] Synthesis of some novel and complex thiopyrano indole derivatives from simple oxindole via intramolecular domino hetero Diels-Alder reactions
    Majumder, Swarup
    Bhuyan, Pulak J.
    TETRAHEDRON LETTERS, 2012, 53 (02) : 137 - 140
  • [37] Domino Knoevenagel-hetero-Diels-Alder reactions: a stereoselective synthesis of sugar-annulated furo[3,2-b] pyrano[4,3-d]pyran derivatives
    Yadav, J. S.
    Reddy, B. V. Subba
    Gopal, A. V. Hara
    Rao, R. Nageshwar
    Somaiah, R.
    Reddy, P. Purushotham
    Kunwar, A. C.
    TETRAHEDRON LETTERS, 2010, 51 (17) : 2305 - 2308
  • [38] Synthesis of new chromeno-annulated cis-fused pyrano[3,4-c]pyran derivatives via domino Knoevenagel-hetero-Diels-Alder reactions and their biological evaluation towards antiproliferative activity
    Venkatesham, A.
    Rao, R. Srinivasa
    Nagaiah, K.
    Yadav, J. S.
    RoopaJones, G.
    Basha, S. J.
    Sridhar, B.
    Addlagatta, A.
    MEDCHEMCOMM, 2012, 3 (06) : 652 - 658
  • [39] Regioselective Synthesis of Chromeno[4′,3′:4,5]pyrano[3,2-c][1,8]naphthyridin-13-one Derivatives by Domino Knoevenagel-Hetero-Diels-Alder Reactions
    Majumdar, K. C.
    Taher, Abu
    Ponra, Sudipta
    SYNTHESIS-STUTTGART, 2011, (22): : 3716 - 3722
  • [40] Synthesis of fused thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels-Alder reaction related tandem and domino processes
    Zelisko, Nataliya
    Atamanyuk, Dmytro
    Ostapiuk, Yuri
    Bryhas, Andriy
    Matiychuk, Vasyl
    Gzella, Andrzej
    Lesyk, Roman
    TETRAHEDRON, 2015, 71 (50) : 9501 - 9508