Modification of the Tiemann rearrangement:: One-pot synthesis of N,N-disubstituted cyanamides from amidoximes

被引：0
|
作者：
Bakunov, SA [1 ]
Rukavishnikov, AV [1 ]
Tkachev, AV [1 ]
机构：
[1] Novosibirsk State Univ, Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
来源：
SYNTHESIS-STUTTGART | 2000年 / 08期
关键词：
Tiemann rearrangement; phase-transfer catalysis; amidoximes; cyanamides; alkylations;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A three-stage one-pot synthetic procedure for transformation of amidoximes to N,N-disubstituted cyanamides in 70-92% yield is described.
引用
收藏
页码：1148 / 1159
页数：12
相关论文
共 50 条
  • [1] Practical Synthesis of N-Substituted Cyanamides via Tiemann Rearrangement of Amidoximes
    Lin, Chia-Chi
    Hsieh, Tsung-Han
    Liao, Pen-Yuan
    Liao, Zhen-Yuan
    Chang, Chih-Wei
    Shih, Yu-Chiao
    Yeh, Wen-Hsiung
    Chien, Tun-Cheng
    ORGANIC LETTERS, 2014, 16 (03) : 892 - 895
  • [2] A simple route to N,N-disubstituted selenoureas from N,N-disubstituted cyanamides
    Keil, D
    Hartmann, H
    SYNTHESIS-STUTTGART, 2004, (01): : 15 - 16
  • [3] One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement
    Wang, Chien-Hong
    Hsieh, Tsung-Han
    Lin, Chia-Chi
    Yeh, Wen-Hsiung
    Lin, Chih-An
    Chien, Tun-Cheng
    SYNLETT, 2015, 26 (13) : 1823 - 1826
  • [4] One-pot synthesis of N,N′-disubstituted acylguanidines
    Zhang, J
    Shi, Y
    Stein, P
    Atwal, K
    Li, C
    TETRAHEDRON LETTERS, 2002, 43 (01) : 57 - 59
  • [5] An improved one-pot cost-effective synthesis of N,N-disubstituted carbamoyl halides and derivatives
    Adeppa, K.
    Rupainwar, D. C.
    Misra, Krishna
    CANADIAN JOURNAL OF CHEMISTRY, 2010, 88 (12) : 1277 - 1280
  • [6] One-pot synthesis of symmetric imidazolium ionic liquids N,N-disubstituted with long alkyl chains
    Damilano, Giacomo
    Kalebic, Demian
    Binnemans, Koen
    Dehaen, Wim
    RSC ADVANCES, 2020, 10 (36) : 21071 - 21081
  • [7] Application of α-chloroaldoxime O-methanesulfonates to one-pot synthesis of N,N′,N"-substituted guanidines via Tiemann rearrangement
    Yamamoto, Yuhei
    Mizuno, Hiroo
    Tsuritani, Takayuki
    Mase, Toshiaki
    TETRAHEDRON LETTERS, 2009, 50 (42) : 5813 - 5815
  • [8] AN IMPROVED METHOD FOR THE DECYANATION OF N,N-DISUBSTITUTED CYANAMIDES
    MISNER, JW
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14): : 3166 - 3168
  • [9] REACTION OF PHENYLLITHIUM WITH SOME N, N-DISUBSTITUTED CYANAMIDES
    ANDERSON, HJ
    WANG, NC
    JWILI, ETP
    CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (13): : 2315 - &
  • [10] ASSISTANCE OF N,N-DISUBSTITUTED AMIDOXIMES IN CYCLODEHYDROGENATION REACTIONS
    MOHRLE, H
    LESSEL, J
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1992, 47 (09): : 1333 - 1340
12345