Titanium(IV)-mediated synthesis of 2,3-diisothiocyanato-succinic acid diesters and 3,6-dithioxo-piperazine derivatives

被引：11
作者：
Ciez, Dariusz [1 ]
机构：
[1] Jagiellonian Univ, Dept Organ Chem, PL-30060 Krakow, Poland
来源：
TETRAHEDRON | 2007年 / 63卷 / 21期
关键词：
D O I：
10.1016/j.tet.2007.03.053
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxidative homocoupling of titanium(IV) enolates of 2-isothiocyanato-carboxylic esters resulted in the synthesis of 2,3-diisothiocyanato-succinic acid diesters. The reactions were carried out using DIPEA/TiCl4 oxidizing system and led to chiral dimers (instead of meso) as main products. Titanium(IV) enolates derived from hindered 2-isothiocyanato-carboxylates did not undergo the oxidative homocoupling but gave 3,6-dithioxo-piperazines. (C) 2007 Elsevier Ltd. All rights reserved.
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页码：4510 / 4515
页数：6
相关论文
共 23 条
[1]  
BINDER H, 1973, Z NATURFORSCH B, VB 28, P530
[2]  
BROCKSOM TJ, 1975, SYNTHESIS-STUTTGART, P396
[3]   BROMOTHIOCYANATION OF ALKENES [J].
CAMBIE, RC ;
LARSEN, DS ;
RUTLEDGE, PS ;
WOODGATE, PD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01) :58-63
[4]   OXIDATIVE CYCLIZATION OF DICARBOXYLATE DIENOLATES AS A NEW CYCLIZATION METHOD [J].
CHUNG, SK ;
DUNN, LB .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1125-1127
[5]   Reactivity of methyl mandelate-Ti(IV)-enediolate:: Oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation [J].
Clerici, A ;
Pastori, N ;
Porta, O .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4174-4176
[6]   REACTIONS OF ETHYLENE DIISOTHIOCYANATE WITH PRIMARY AND SECONDARY AMINES [J].
DANGELI, F ;
GIORMANI, V ;
BANDEL, A .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1596-&
[7]   ISOTHIOCYANATES AND THEIR SYNTHETIC PRODUCERS .11. SYNTHESIS AND PROPERTIES OF ALKYL ISOTHIOCYANATOCARBOXYLATES [J].
FLOCH, L ;
KOVAC, S .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1975, 40 (09) :2845-2854
[8]   CHEMISTRY OF CERTAIN THIOCYANATES AND ISOTHIOCYANATES CONTAINING SILICON [J].
GLOWACKI, GR ;
POST, HW .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (02) :634-&
[9]  
GRISHCHUK BD, 1994, PHARM CHEM J, V28, P39
[10]  
INABA SI, 1977, TETRAHEDRON LETT, P2009
123