A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent

被引：40
|
作者：
Xiong, Xingquan [1 ]
Yi, Chao [1 ]
Liao, Xu [1 ]
Lai, Shilin [1 ]
机构：
[1] Univ Huaqiao, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 05期
基金：
中国国家自然科学基金;
关键词：
5-Substituted-1H-tetrazoles; Aldehydes; One-pot synthesis; Deep eutectic solvent; Green chemistry; 5-SUBSTITUTED; 1H-TETRAZOLES; 3+2 CYCLOADDITION; RECYCLABLE CATALYST; EFFICIENT SYNTHESIS; REUSABLE CATALYST; N-ARYLATION; NITRILES; NANOPARTICLES; COMPLEX; HETEROCYCLES;
D O I：
10.1016/j.tetlet.2018.12.037
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 5-substituted-1H-tetrazoles have been efficiently synthesized in moderate to excellent yields (68-90%) under mild reaction conditions by combining aryl aldehydes, hydroxylamine hydrochloride with sodium azide in the presence of catalytic amount of Cu(OAc)(2) in deep eutectic solvent (DES). The new synthetic method has many advantages, such as high conversion, green reaction medium, easy work-up, low cost, and environment friendly. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：402 / 406
页数：5
相关论文
共 50 条
  • [21] Nano TiO2-H3BO3 as an efficient and recycable catalyst for the synthesis of 5-substituted-1H-tetrazoles
    Abrishami, Fatemeh
    Ebrahimikia, Maryam
    Rafiee, Fatemeh
    IRANIAN JOURNAL OF CATALYSIS, 2018, 8 (02): : 103 - 111
  • [22] CuO/aluminosilicate as an efficient heterogeneous nanocatalyst for the synthesis and sequential one-pot functionalization of 5-substituted-1H-tetrazoles
    Movaheditabar, Parviz
    Javaherian, Mohammad
    Nobakht, Valiollah
    REACTION KINETICS MECHANISMS AND CATALYSIS, 2017, 122 (01) : 217 - 228
  • [23] ZSM-5 catalyzed one pot three-component synthesis of 5-substituted-1H-tetrazoles from aldehyde
    Hatvate, Navnath T.
    Ghodse, Shrikant M.
    Telvekar, Vikas N.
    SYNTHETIC COMMUNICATIONS, 2019, 49 (24) : 3553 - 3559
  • [24] Non-catalyzed addition of heterocyclic thiols and 5-substituted-1H-tetrazoles to vinyl ethers
    Melnikova, Iuliia
    Roh, Jaroslav
    Kunes, Jiri
    Artamonova, Tatiana
    Zevatskii, Yuri
    Myznikov, Leonid
    TETRAHEDRON LETTERS, 2017, 58 (40) : 3842 - 3845
  • [25] NANO SILICA BORON SULFURIC ACID AS A DUAL BRONSTED/LEWIS SOLID ACID FOR THE SYNTHESIS OF 5-SUBSTITUTED-1H-TETRAZOLES
    Yazdanian, Motahareh
    Javaherian, Mohammad
    Hamadi, Hosein
    HETEROCYCLIC LETTERS, 2018, 8 (02): : 277 - 285
  • [26] Synthesis of 5-substituted-1H-tetrazoles using zinc zirconium phosphate and copper zirconium phosphate as reusable heterogeneous catalysts
    Fatemeh Abrishami
    Marzieh Daryanavard
    Fatemeh Nakhaei
    Journal of the Iranian Chemical Society, 2023, 20 : 1821 - 1829
  • [27] 4-(N,N-Dimethylamino)pyridinium acetate as a recyclable catalyst for the synthesis of 5-substituted-1H-tetrazoles
    Nowrouzi, Najmeh
    Farahi, Soghra
    Irajzadeh, Maryam
    TETRAHEDRON LETTERS, 2015, 56 (05) : 739 - 742
  • [28] Synthesis of 5-substituted-1H-tetrazoles using zinc zirconium phosphate and copper zirconium phosphate as reusable heterogeneous catalysts
    Abrishami, Fatemeh
    Daryanavard, Marzieh
    Nakhaei, Fatemeh
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2023, 20 (08) : 1821 - 1829
  • [29] CuO/aluminosilicate as an efficient heterogeneous nanocatalyst for the synthesis and sequential one-pot functionalization of 5-substituted-1H-tetrazoles
    Parviz Movaheditabar
    Mohammad Javaherian
    Valiollah Nobakht
    Reaction Kinetics, Mechanisms and Catalysis, 2017, 122 : 217 - 228
  • [30] Expanded perlite: an inexpensive natural efficient heterogeneous catalyst for the green and highly accelerated solvent-free synthesis of 5-substituted-1H-tetrazoles using [bmim]N3 and nitriles
    Jahanshahi, Roya
    Akhlaghinia, Batool
    RSC ADVANCES, 2015, 5 (126) : 104087 - 104094
12345