Reactions of 1,1,4,4-tetramethylsemicarbazide with prop-2-ynyl bromide, allyl bromide, and 1,3-dibromoprop-1-yne

被引：1
|
作者：
Elokhina, V. N. [1 ]
Nakhmanovich, A. S. [1 ]
Abramova, E. V. [1 ]
Larina, L. I. [1 ]
机构：
[1] Russian Acad Sci, Favorskii Irkutsk Inst Chem, Siberian Div, Irkutsk 664033, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 42卷 / 10期
关键词：
Semicarbazide; Allyl Bromide; Methylhydrazine; Tertiary Nitrogen Atom; Dimethylhydrazones;
D O I：
10.1134/S1070428006100022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1, 1,4,4-Tetramethylsemicarbazide readily undergoes alkylation with prop-2-ynyl bromide and allyl bromide at the tertiary nitrogen atom of the hydrazine fragment to give 1-(prop-2-yn-1-yl)- and 1-(prop-2-en-1-yl) -1,1-dimethyl-2-(dimethylannocarbonyl)hydrazinium bromides, respectively. A new procedure was proposed for the synthesis of 6-bromomethylidene-2-dimethylamino-4,4-dimethyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-ium bromide by reaction of 1, 1,4,4-tetramethylsemicarbazide with 1,3-dibromoprop-1-yne in acetonitrile.
引用
收藏
页码：1426 / 1428
页数：3
相关论文
共 50 条
  • [21] ELECTROPHILIC ADDITION REACTIONS OF 1,1 DIMETHYLDIAZENIUM BROMIDE WITH 1,3 DIENES + STYRENES
    URRY, WH
    IKOKU, C
    MOORE, DW
    SZECSI, P
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (11) : 2224 - &
  • [22] (E)-1,1,4,4-Tetraphenylbut-2-yne-1,4-diol
    Sundar, J. Kalyana
    Kumar, K. Mohan
    Vijayakumar, V.
    Suresh, J.
    Natarajan, S.
    Lakshman, P. L. Nilantha
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O679 - U5550
  • [23] [1,3]-Dipolar cycloaddition of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)-1H-indole
    Durust, Yasar
    Sagirli, Akin
    Kariuki, Benson M.
    Knight, David W.
    TETRAHEDRON, 2014, 70 (35) : 6012 - 6019
  • [24] Carbonyl propargylation by 1-substituted prop-2-ynyl mesylates and carbonyl allenylation by 3-substituted prop-2-ynyl mesylates with tin(II) iodide and tetrabutylammonium iodide
    Masuyama, Y
    Watabe, A
    Ito, A
    Kurusu, Y
    CHEMICAL COMMUNICATIONS, 2000, (20) : 2009 - 2010
  • [25] POLAR ADDITION OF HYDROGEN BROMIDE TO OLEFINS .2. HYDROGEN BROMIDE ADDITION TO 1,1,4,4-TETRAMETHYL-1,4-DIHYDRONAPHTHALENE - MECHANISTIC STUDIES
    NAAB, P
    STAAB, HA
    CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (08): : 2982 - 2996
  • [26] 4-Methyl-N-(prop-2-ynyl)-N-(1H-pyrrol-2-ylmethyl)-benzenesulfonamide
    Bats, JW
    Weyrauch, JP
    Hashmi, ASK
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2002, 58 : o290 - o292
  • [27] 5-Nitro-1,3-bis(prop-2-ynyl)-1H-1,3-benzimidazol-2(3H)-one
    Rodi, Youssef Kandri
    Misbahi, Khalid
    EI-Ghayoury, Abdelkrim
    Zorina, Leokadiya
    Essassi, El Mokhtar
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1159 - +
  • [28] 1,3-THIAZINES .19. PREPARATION OF N-MONOSUBSTITUTED PROP-2-YNYL CARBONAMIDOTHIOATES AND ATTEMPTS TO CYCLIZE THESE PRODUCTS
    HANEFELD, W
    ARCHIV DER PHARMAZIE, 1982, 315 (04) : 364 - 367
  • [29] Alkylation of 1-(prop-2-ynyl)piperidine with СН-acids in ihe presence of mercury(II) acetate
    N. G. Hobosyan
    K. V. Balyan
    A. L. Petrosyan
    S. A. Hovakimyan
    Zh. A. Chobanyan
    R. S. Nersisyan
    Russian Journal of General Chemistry, 2017, 87 : 29 - 32
  • [30] Prop-2-ynyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate
    Temelkoff, DP
    Norris, P
    Zeller, M
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O2273 - O2274
12345