Synthesis of polyfunctionally substituted benzo[5,6]chromeno[4,3,2-de][1,6]naphthyridines and 5H-benzo[5,6]chromeno[3,4-c]pyridines

被引：0
|
作者：
Shaker, Raafat M. [1 ]
机构：
[1] El Minya Univ, Fac Sci, Dept Chem, El Minya, Egypt
来源：
ARKIVOC | 2006年
关键词：
heterocyclic o-aminonitriles; chromenes; 1,6-naphthyridines;
D O I：
10.3998/ark.5550190.0007.e09
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclocondensation of 2-(3-amino-2-cyano-1H-benzo[f]chromen-1-yl)-malononitrile (1) with beta-dicarbonyles 2a-d, benzoylacetonitrile 2e, malononitrile 2f, and 3-aminocrotononitrile ( 9) gave the benzo[ 5,6] chromeno[ 4,3,2- de][ 1,6] naphthyridines (4a-e, 6 and 11). Refluxing 1 with ammonium acetate in ethanol gave pyridine-3,5-dicarbonitrile 12 that converted in the presence of HCl into 5H-benzo[ 5,6] chromeno-[3,4-c] pyridine 14. The structures of the products were proved by elemental analyses, IR, MS, H-1 and C-13 NMR spectroscopy.
引用
收藏
页码：59 / 67
页数：9
相关论文
共 50 条
  • [1] Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED
    Ryzhkova, Yuliya E.
    Ryzhkov, Fedor, V
    Fakhrutdinov, Artem N.
    Elinson, Michail N.
    MOLECULES, 2022, 27 (13):
  • [2] SYNTHESIS OF PYRIDO[3',2'/5,6]PYRANO[4,3,2-DE]QUINOLINE
    FUJIWARA, H
    OKABAYASHI, I
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (06) : 1163 - 1165
  • [3] PREPARATION OF PYRIDO[3',2'/5,6]THIOPYRANO[4,3,2-DE]-QUINOLINE
    FUJIWARA, H
    OKABAYASHI, I
    HETEROCYCLES, 1993, 36 (05) : 1105 - 1113
  • [4] Synthesis of tetracyclic 4H-benzo[5,6]chromeno[3,4-d]oxazoles via palladium-catalyzed intramolecular direct heteroarylation
    Kumar, Sujeet
    Kajol, Km
    Nayak, Prakash
    Kumar, Amit
    Ramesh, Chintakunta
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (03)
  • [5] Synthesis and antibacterial activity of some new benzo[5,6]chromeno[2,3-d]pyrimidines
    Shohreh Ameli
    Mehdi Pordel
    Abolghasem Davoodnia
    Maryam Jajarmi
    Russian Journal of Bioorganic Chemistry, 2017, 43 : 429 - 434
  • [6] Synthesis and characteristics of novel fluorescence dyes based on chromeno[4,3,2-de][1,6]naphthyridine framework
    Wang, Haiying
    Shi, Jingjing
    Wang, Chao
    Zhang, Xiaoxiao
    Zhao, Lingling
    Wan, Yu
    Wu, Hui
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2013, 103 : 62 - 67
  • [7] Synthesis and Antibacterial Activity of Some New Benzo[5,6] chromeno[2,3-d] pyrimidines
    Ameli, Shohreh
    Pordel, Mehdi
    Davoodnia, Abolghasem
    Jajarmi, Maryam
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2017, 43 (04) : 429 - 434
  • [8] A Convenient and Facile Synthesis of Isoxazolyl-chromeno[4,3,2-de]pyrimido[4,5-h][1,6]napthyridinones
    Rajanarendar, Eligeti
    Ramakrishna, Saini
    Kishore, Baireddy
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (05) : 1415 - 1420
  • [9] Novel fluorescence dyes based on entirely new chromeno[4,3,2-de][1,6]naphthyridine framework
    Wang, Hai-Ying
    Shi, Jing-Jing
    Wang, Chao
    Zhang, Xiao-Xiao
    Wan, Yu
    Wu, Hui
    DYES AND PIGMENTS, 2012, 95 (02) : 268 - 274
  • [10] Organocatalytic approach toward the green one-pot synthesis of novel benzo[f]chromenes and 12H-benzo[5,6]chromeno[2,3-b]pyridines
    Abolfazl Olyaei
    Mohammad Sadegh Shahsavari
    Mahdieh Sadeghpour
    Research on Chemical Intermediates, 2018, 44 : 943 - 956
12345