One-pot sequential regioselective intramolecular synthesis of furo[3,2-c]chromen and imidazo[1,2-a]pyridine via catalyst-free and basic conditions

被引:0
|
作者
Yadav, Maruti B. [1 ]
Yeon, Tae Jeong [1 ]
机构
[1] Pukyong Natl Univ, Dept Image Sci & Engn, Busan 608737, South Korea
关键词
CASCADE REACTIONS; 3-COMPONENT REACTION; EFFICIENT; INHIBITORS; COUMARINS; FUROCOUMARINS; DERIVATIVES; CYCLIZATION; ANNULATION; PYRIDINES;
D O I
10.1002/jhet.4735
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We developed a sequential intramolecular ring-closure-opening-closure pathway using a catalyst-free and organo-base catalyzed system for the synthesis of fused regioselective tricyclic furo[3,2-c]chromen and bicyclic imidazo[1,2-a]pyridine via a one-pot three-component reaction. The protocol involved a Knoevenagel and Michael adduct via intramolecular cyclization with 4-hydroxycoumarin, aromatic glyoxal, and 2-aminopyridine under heating and ambient conditions with very good yields. The merits of this methodology were studied, and new practical ways were developed to access furo[3,2-c]chromen and imidazo[1,2-a]pyridine moieties. Regioselective Intramolecular Synthesis of Furo[3,2-c]chromen and Imidazo[1,2-a]pyridine derivatives.image
引用
收藏
页码:2053 / 2062
页数:10
相关论文
共 50 条
  • [11] Catalyst-free concise synthesis of imidazo[1,2-a]pyrrolo[3,4-e]pyridine derivatives
    Chen, Xuebing
    Zhu, Li
    Fang, Li
    Yan, Shengjiao
    Lin, Jun
    RSC ADVANCES, 2014, 4 (20) : 9926 - 9934
  • [12] Catalyst-free synthesis of imidazo [1,2-a] pyridines via Groebke multicomponent reaction
    Najmedin Azizi
    Sahar Dezfooli
    Environmental Chemistry Letters, 2016, 14 : 201 - 206
  • [13] Catalyst-free synthesis of imidazo [1,2-a] pyridines via Groebke multicomponent reaction
    Azizi, Najmedin
    Dezfooli, Sahar
    ENVIRONMENTAL CHEMISTRY LETTERS, 2016, 14 (02) : 201 - 206
  • [14] Solvent-free and efficient synthesis of imidazo[1,2-a]pyridine derivatives via a one-pot three-component reaction
    Wen, Li-Rong
    Li, Zhao-Rui
    Li, Ming
    Cao, Han
    GREEN CHEMISTRY, 2012, 14 (03) : 707 - 716
  • [15] Synthesis of 2-phosphonylated imidazo[1,2-a]pyridines under catalyst-free conditions
    Krylov, Aleksandr S.
    Kaskevich, Ksenia I.
    Erkhitueva, Elena B.
    Svintsitskaya, Nataly I.
    Dogadina, Albina V.
    TETRAHEDRON LETTERS, 2018, 59 (49) : 4326 - 4329
  • [16] DABCO-catalysed one-pot synthesis of furo[3,2-c]coumarin from 3-halochromone
    Maiti, Sourav
    Ghosh, Jaydip
    Sarkar, Tapas
    Bandyopadhyay, Chandrakanta
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2013, 90 (09) : 1497 - 1499
  • [17] Catalyst-free one-pot synthesis of benzimidazoles from 1,2-diaminoarenes and alcohols
    Marri, Mahender Reddy
    Peraka, Swamy
    Macharla, Arun Kumar
    Mameda, Naresh
    Kodumuri, Srujana
    Nama, Narender
    TETRAHEDRON LETTERS, 2014, 55 (48) : 6520 - 6525
  • [18] Catalyst-free rapid synthesis of benzo[4,5]imidazo[1,2-a]-pyrimidine-3-carboxamides via four-component coupling in one pot
    Shaabani, Ahmad
    Seyyedhamzeh, Mozhdeh
    Ganji, Nasim
    Seik Weng Ng
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2014, 11 (02) : 481 - 487
  • [19] Catalyst-free rapid synthesis of benzo[4,5]imidazo[1,2-a]-pyrimidine-3-carboxamides via four-component coupling in one pot
    Ahmad Shaabani
    Mozhdeh Seyyedhamzeh
    Nasim Ganji
    Seik Weng Ng
    Journal of the Iranian Chemical Society, 2014, 11 : 481 - 487
  • [20] Lanthanide chloride catalyzed imino Diels-Alder reaction.: One-pot synthesis of pyrano[3,2-c]- and furo[3,2-c] quinolines
    Ma, Y
    Qian, CT
    Xie, MH
    Sun, J
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17): : 6462 - 6467