Direct synthesis of dithioketals from N,N-dialkylhydrazones

被引：21
|
作者：
Diez, E
Lopez, AM
Pareja, C
Martin, E
Fernandez, R
Lassaletta, JM
机构：
[1] Univ Sevilla, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain
[2] USE, CSIC, Inst Invest Quim, E-41092 Seville, Spain
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 43期
关键词：
D O I：
10.1016/S0040-4039(98)01728-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Direct dithioketalisation of N,N-dialkylhydrazones promoted by BF3. Et2O or p-TsOH and 1,2-ethanedithiol in dry medium affords the corresponding dithiolanes in nearly quantitative yields. A variety of hydrazones derived from several kinds of aldehydes (aliphatic, aromatic, and alpha,beta-unsaturated) and hydrazines [N, N-dimethylhydrazine, 1-aminopyrrolidine, and (S)-1-amino-2- (methoxymethyl)pyrrolidine (SAMP)] were reacted, indicating the generality of the method. The reaction was demonstrated to proceed without racemization of a particularly sensitive chiral substrate. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7955 / 7958
页数：4
相关论文
共 50 条
  • [21] Michael addition of chiral formaldehyde N,N-dialkylhydrazones to activated cyclic alkenes
    Vázquez, J
    Cristea, E
    Díez, E
    Lassaletta, JM
    Prieto, A
    Fernández, R
    TETRAHEDRON, 2005, 61 (16) : 4115 - 4128
  • [22] A general photoinduced electron transfer-directed chemoselective perfluoroalkylation of N,N-dialkylhydrazones
    Xie, Jin
    Li, Jian
    Wurm, Thomas
    Weingand, Vanessa
    Sung, Hui-Ling
    Rominger, Frank
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (07): : 841 - 845
  • [23] Studies on stereoselective [2+2] cycloadditions between N,N-dialkylhydrazones and ketenes
    Martín-Zamora, E
    Ferrete, A
    Llera, JM
    Muñoz, JM
    Pappalardo, RR
    Fernández, R
    Lassaletta, JM
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) : 6111 - 6129
  • [24] N,N-Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion-Binding Catalysis
    Gomez-Martinez, Melania
    del Carmen Perez-Aguilar, Maria
    Piekarski, Dariusz G.
    Daniliuc, Constantin G.
    Garcia Mancheno, Olga
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (10) : 5102 - 5107
  • [25] Enantioselective synthesis of 4-unsubstituted 3-alkoxy- and 3-aminoazetidin-2-ones from formaldehyde N,N-dialkylhydrazones
    Fernández, R
    Ferrete, A
    Lassaletta, JM
    Llera, JM
    Monge, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (16) : 2893 - 2897
  • [26] Asymmetric Mannich-type addition of ketene silyl acetals and thioacetals to N,N-dialkylhydrazones
    Díez, E
    Prieto, A
    Simon, M
    Vázquez, J
    Alvarez, E
    Fernández, R
    Lassaletta, JM
    SYNTHESIS-STUTTGART, 2006, 3 (03): : 540 - 550
  • [27] Continuous Flow α-Arylation of N,N-Dialkylhydrazones under Visible-Light Photoredox Catalysis
    Vega, Juan A.
    Manuel Alonso, Jose
    Mendez, Gabriela
    Ciordia, Myriam
    Delgado, Francisca
    Trabanco, Andres A.
    ORGANIC LETTERS, 2017, 19 (04) : 938 - 941
  • [28] Electrocatalytic dehydrogenative and defluorinative coupling between aldehyde-derived N,N-dialkylhydrazones and fluoromalonates: synthesis of 2-pyrazolines
    Noel, Florent
    El Kaim, Laurent
    Masson, Geraldine
    Claraz, Aurelie
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (21) : 4269 - 4273
  • [29] THE WOLFF-KISHNER REDUCTION .1. THE PREPARATION AND PROPERTIES OF N-ALKYL-AND N,N-DIALKYLHYDRAZONES
    TODD, D
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (04) : 1353 - 1355
  • [30] N,N-dialkylhydrazones as the imine component in the Staudinger-like [2+2] cycloaddition to benzyloxyketene
    Fernández, R
    Ferrete, A
    Lassaletta, JM
    Liera, JM
    Martín-Zamora, E
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (05) : 831 - +
12345