Copper catalyzed cyclopropanation of 1,2,3,4-tetrahydropyridin-2-ones with trimethylsilyldiazomethane: A facile and selective synthesis of 2-aza-3-oxobicyclo[4.1.0] heptanes

被引：0
|
作者：
Sharma, VB [1 ]
Jain, SL [1 ]
Sain, B [1 ]
机构：
[1] Indian Inst Petr, Chem & Biotechnol Div, Dehra Dun 248005, Uttar Pradesh, India
来源：
HETEROCYCLES | 2006年 / 68卷 / 03期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactions of a series of 1,2,3,4-tetrahydropyridin-2-ones with trimethylsilyldiazomethane using catalytic amounts of copper(II) triflate in refluxing 1,2-dichloroethane yielded exclusively 3-oxo-2-azabicyclo[4.1.0]-heptanes in good yields. The application of ultrasonic radiation enhanced the reaction rate and allowed the reactions to be conducted at room temperature.
引用
收藏
页码：475 / 481
页数：7
相关论文
共 50 条
  • [21] A FACILE SYNTHESIS AND NOVEL REACTIONS OF 1,2,3,4-PENTATETRAENE EPISULFIDES
    TOKITOH, N
    SUZUKI, T
    ANDO, W
    TETRAHEDRON LETTERS, 1989, 30 (32) : 4271 - 4274
  • [22] Palladium(O)-catalyzed asymmetric synthesis of 1,2,3,4-tetrahydro-2-vinylquinoxalines
    Massacret, M
    Lhoste, P
    Sinou, D
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (01) : 129 - 134
  • [23] Mg(ClO4)2 as a powerful catalyst for synthesis of 1,2,3,4-tetrahydropyrimidin-2-ones
    Chen, WY
    Lu, J
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (09) : 1111 - 1113
  • [24] Copper-Catalyzed One-Pot Synthesis of 2-Alkylidene-1,2,3,4-tetrahydropyrimidines
    Lu, Wei
    Song, Wangze
    Hong, Deng
    Lu, Ping
    Wang, Yanguang
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) : 1768 - 1772
  • [25] SYNTHESIS OF 3-OXABICYCLO[3,1,1]HEPTANES BY REARRANGEMENT OF 2-OXASPIRO[3,3]HEPTANES
    COCHRANE, WP
    PAUSON, PL
    STEVENS, TS
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (17): : 2346 - &
  • [26] A SIMPLE SYNTHESIS OF 1,2,3,4-TETRAHYDROPHENANTHRENONE AND 1,2,3,4-TETRAHYDROCHRYSENONE DERIVATIVES
    LAKHVICH, FA
    KHLEBNICOVA, TS
    AKHREM, AA
    SYNTHESIS-STUTTGART, 1985, (08): : 784 - 786
  • [27] Facile and Selective Synthesis of 2-Substituted Benzimidazoles Catalyzed by FeCl3/Al2O3
    Chen, Guo-Feng
    Dong, Xiao-Yun
    E-JOURNAL OF CHEMISTRY, 2012, 9 (01) : 289 - 293
  • [28] Synthesis of 3-aryl-1,2,3,4-tetrahydrobenzo[f]quinolin-1-ones
    Kozlov, NG
    Basalaeva, LI
    Tychinskaya, LY
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 36 (09) : 1360 - 1364
  • [29] A convergent synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones
    Cholleton, N
    Zard, SZ
    TETRAHEDRON LETTERS, 1998, 39 (40) : 7295 - 7298
  • [30] Phosphine-Catalyzed [3+2] Cycloaddition of Aza-Aurones and Allenoates: Enantioselective Synthesis of 2-Spirocyclopentyl-Indolin-3-Ones
    Brambilla, Elisa
    Pozza, Camilla
    Rizzato, Silvia
    Abbiati, Giorgio
    Pirovano, Valentina
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (03)
12345