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
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