Clean and Green Approach for One-pot Synthesis of Pyrazines from Ethylenediamine and 1, 2-Diketone or Its Analogues Under Neat Reaction Condition

被引:1
|
作者
Ghosh, Pranab [1 ]
Chakraborty, Rakesh Ranjan [1 ]
机构
[1] Univ North Bengal, Dept Chem, Raja Rammohanpur, W Bengal, India
关键词
1,2-Diketone; ethylenediamine; environmentally benign process; pyrazine; moieties; column chromatography; QUINOXALINES; EFFICIENT; ANTS;
D O I
10.2174/1570178614666170609072519
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Background: Compounds having N-heterocyclic moieties are of huge importance in the field of agrochemical, pharmaceutical, biological, fragrances, etc. Due to a lot of applications associated with pyrazine moieties, their synthesis has always been important for organic chemists. Method: Surfeit synthetic methodologies are documented in literature. Most of the methodologies used expensive solvents, harmful metal catalyst and all suffer from rigorous work-up procedures. An efficient, environmentally benign methodology, needs to be developed. We mixed ethylenediamine (2mmol) with 1,2-diketone(1mmol), later, alpha-hydroxy ketone and alpha-bromo ketone on magnetic stirrer at room temperature under neat reaction condition for 5 to 10 hrs. Results: After purification by column chromatography using silica gel(60-120 mesh) and pet-ether, ethylacetate mixture as eluent, we achieved pyrazine derivatives from moderate to high yield. Conclusion: Efficient and clean procedure for one-pot preparation of pyrazines from ethylenediamine and 1,2-diketones or with alpha-hydroxy ketone or with alpha-bromo ketone has been carried out under neat reaction condition at room temperature. Environmentally benign process furnishing moderate to excellent yields of the product and simple work-up giving pure products are special features of this reaction.
引用
收藏
页码:566 / 570
页数:5
相关论文
共 50 条
  • [31] Green Synthesis of 1,2,4,5-Tetrasubstituted and 2,4,5-Trisubstituted Imidazole Derivatives Involving One-pot Multicomponent Reaction
    Bansal, Ravi
    Soni, Pradeep K.
    Halve, Anand K.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (06) : 1308 - 1312
  • [32] A sequential one-pot approach to 1,2,4,5-tetrasubstituted-2H-imidazole synthesis from disubstituted alkynes
    Boominathan, Siva Senthil Kumar
    Chen, Chung-Yu
    Huang, Po-Jui
    Hou, Ruei-Jhih
    Wang, Jeh-Jeng
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (09) : 6914 - 6918
  • [33] One-Pot Synthesis of 1,4-Oxathiino[2,3-b]quinoxalines or -pyrazines from 2,3-Dichloroquinoxaline or -pyrazine and 1-Aryl-2-bromoalkan-1-ones
    Kobayashi, Kazuhiro
    Konishi, Natsuki
    Suzuki, Teruhiko
    Nakagawa, Kazuhiro
    HELVETICA CHIMICA ACTA, 2013, 96 (08) : 1452 - 1456
  • [34] Nano-cell-OBF2: an efficient and cheap catalyst for one-pot synthesis of pyrano[4,3-b]pyrans under mild and green condition
    Khatat, Saeed Mousavi
    Sadeghi, Bahareh
    Ghasemi, Maryam
    INORGANIC AND NANO-METAL CHEMISTRY, 2019, 49 (02) : 56 - 62
  • [35] One-pot synthesis of phenazines from 2-naphthols with 1, 2-diamines and its biological importance and binding studies
    Raju Gajula
    Vijayacharan Guguloth
    Satyanarayana Battu
    Journal of Chemical Sciences, 2021, 133
  • [36] Synthesis of 3,4-dihydropyrimidin-2(1H)-one via one-pot Biginelli reaction under solvent-free conditions
    Huan Peng
    Yulin Hu
    Rong Xing
    Dong Fang
    Monatshefte für Chemie - Chemical Monthly, 2015, 146 : 2053 - 2058
  • [37] Synthesis of 3,4-dihydropyrimidin-2(1H)-one via one-pot Biginelli reaction under solvent-free conditions
    Peng, Huan
    Hu, Yulin
    Xing, Rong
    Fang, Dong
    MONATSHEFTE FUR CHEMIE, 2015, 146 (12): : 2053 - 2058
  • [38] One-pot synthesis of phenazines from 2-naphthols with 1, 2-diamines and its biological importance and binding studies
    Gajula, Raju
    Guguloth, Vijayacharan
    Battu, Satyanarayana
    JOURNAL OF CHEMICAL SCIENCES, 2021, 133 (02)
  • [39] One-pot synthesis of 1,2,4-oxadiazoles from chalcogen amino acid derivatives under microwave irradiation
    Wolf, Lucas
    Mayer, Joao C. P.
    Quoos, Natalia
    Sauer, Andre C.
    Schwab, Ricardo S.
    Rodrigues, Oscar E. D.
    Dornelles, Luciano
    TETRAHEDRON, 2021, 91
  • [40] Efficient Synthesis of 1-Amidoalkyl-2-Naphthols by One-Pot, Three-Component Reaction under Solvent-Free conditions
    Karimi-Jaberi, Zahed
    Jokar, Marziyeh
    Abbasi, S. Zoleykha
    JOURNAL OF CHEMISTRY, 2013, 2013