Synthesis of 1,2,4-Triazolines: Base-Catalyzed Hydrazination/Cyclization Cascade of α-Isocyano Esters and Amides

被引：71
|
作者：
Monge, David [1 ]
Jensen, Kim L. [1 ]
Marin, Irene [1 ]
Jorgensen, Karl Anker [1 ]
机构：
[1] Aarhus Univ, Ctr Catalysis, DK-8000 Aarhus C, Denmark
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 02期
关键词：
BOND-FORMING REACTIONS; DIELS-ALDER REACTION; DIETHYL AZODICARBOXYLATE; MULTICOMPONENT REACTION; MITSUNOBU REACTION; DERIVATIVES; OXAZOLES; 4-PHENYL-3H-1,2,4-TRIAZOLE-3,5(4H)-DIONE; REACTIVITY; STRATEGY;
D O I：
10.1021/ol102812c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient, efficient synthesis of 1,2,4-triazolines from alpha-isocyano esters/amides and azodicarboxylates is presented. The developed reaction cascade is based on a base-catalyzed hydrazination-type reaction followed by a subsequent cyclization providing the triazolines in good to excellent yields (75-99%). Phosphine-catalyzed and preliminary asymmetric phase-transfer catalysis approaches have also been investigated.
引用
收藏
页码：328 / 331
页数：4
相关论文
共 33 条
  • [21] Efficient Synthesis of 2-Amino-1-Arylethanols Through a Lewis Base-Catalyzed SiCl4-Mediated Asymmetric Passerini-Type Reaction
    Gernet, Aurelie
    Ratovelomanana-Vidal, Virginie
    Pirat, Jean-Luc
    Virieux, David
    Ayad, Tahar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (41) : 6497 - 6500
  • [22] Base-catalyzed cyclization reaction of 2-chloroquinoline-3-carbonitriles and guanidine hydrochloride: a rapid synthesis of 2-amino-3H-pyrimido[4,5-b] quinolin-4-ones
    Chandra, Atish
    Upadhyay, Shraddha
    Singh, Bhawana
    Sharma, Neha
    Singh, Radhey M.
    TETRAHEDRON, 2011, 67 (47) : 9219 - 9224
  • [23] Copper-Catalyzed Cascade Acylation/Coupling Cyclization Process for the Synthesis of Polycyclic Fused Imidazo[2,1-b][1,3]thiazinones
    Wang Zhiming
    Yu Bin
    Zhang Xiuqin
    Sun Xiaoqiang
    Bao Weiliang
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (12) : 2775 - 2780
  • [24] KI-catalyzed oxidative cyclization of -keto acids and 2-hydrazinopyridines: efficient one-pot synthesis of 1,2,4-triazolo[4,3-a]pyridines
    Yang, De-Suo
    Wang, Juan
    Gao, Peng
    Bai, Zi-Jing
    Duan, Dong-Zhu
    Fan, Ming-Jin
    RSC ADVANCES, 2018, 8 (57): : 32597 - 32600
  • [25] Base-Catalyzed Domino Reaction Between Aldoxime and N- Chlorosuccinimide in Alcohol: One-Pot Synthesis of Alkyl 3-(3-Aryl-1,2,4-oxadiazol-5-yl)propanoates
    Chilaka, Sai Krishna
    Chellu, Ramesh Kumar
    Soda, Anil Kumar
    Kurva, Srinivas
    Nanubolu, Jagadeesh Babu
    Madabhushi, Sridhar
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (17) : 2944 - 2950
  • [26] Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a] indoles via NaI-catalyzed cascade radical addition/cyclization/isomerization
    Zhang, Pengbo
    Gao, Yuzhen
    Chen, Su
    Tang, Guo
    Zhao, Yufen
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1350 - 1353
  • [27] Enantioselective Synthesis of 4-Substituted 4,5-Dihydro-1H-[1,5]benzodiazepin-2(3H)-ones by the Lewis Base-Catalyzed Hydrosilylation
    Chen, Xing
    Zheng, Yongsheng
    Shu, Chang
    Yuan, Weicheng
    Liu, Bo
    Zhang, Xiaomei
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) : 9109 - 9115
  • [28] Base-catalyzed synthesis of 2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-ones and isolation of intermediates using microwave irradiation
    Davoodnia, A.
    Bakavoli, M.
    Zareei, N.
    Tavakoli-Hoseini, N.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2009, 41 (03): : 226 - 229
  • [29] Copper-catalyzed tandem aerobic oxidative cyclization for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters
    An, Zhenyu
    Jiang, Yong
    Guan, Xin
    Yan, Rulong
    CHEMICAL COMMUNICATIONS, 2018, 54 (76) : 10738 - 10741
  • [30] Cu(I)-Catalyzed and Base-Promoted [5+2+1] Cascade Cyclization of 2-Nitrochalcones with Aliphatic Primary Amines to 5H-Pyrimido[5,4-b]indole Frameworks
    Wu, Qin
    Xu, Genrui
    Li, Weiqiang
    Wan, Juan
    Liu, Teng
    Huang, Chao
    ORGANIC LETTERS, 2022, 24 (22) : 3950 - 3954
1234