Uncatalyzed One-Pot Synthesis of Highly Substituted Pyridazines and Pyrazoline-Spirooxindoles via Domino SN/Condensation/Aza-ene Addition Cyclization Reaction Sequence

被引：23
|
作者：
Zohreh, Nasrin [1 ]
Alizadeh, Abdolali [1 ]
机构：
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
来源：
ACS COMBINATORIAL SCIENCE | 2013年 / 15卷 / 06期
关键词：
1,2-diaza heterocycles; spirooxindole; pyrazoline; pyridazine; one-pot reactions; domino reactions; nitro ketene dithioacetal; isatin; benzil; 1,2-dicarbonyls; aza-ene reaction; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; CONSTRUCTION; DERIVATIVES; INHIBITORS; CHEMISTRY; DISCOVERY; ISATINS; FACILE; ENTRY;
D O I：
10.1021/co400005y
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A previously unknown class of highly substituted pyridazines and pyrazoline-spirooxinoles are easily prepared by an uncatalyzed one-pot three-component approach incorporating a domino SN/condensation/aza-ene addition cyclization reaction sequence. 1,1-Dihydrazino-2-nitroethylene (DHNE) which is generated in situ from the nudeophilic substitution (SN) reaction of hydrazine and 1,1-bis(methylthio)-2-nitroethylene (BMTNE), allowed to be condensed with active 1,2-dicarbonyl compounds followed by an intramolecular aza-ene addition cyclization to obtain the titled products depending on the type of 1,2-dicarbonyl. All reactions are easily performed and proceed with high efficiency under very simple and mild conditions without any catalyst and give good yields avoiding time-consuming, costly syntheses, and tedious workup and purification of products.
引用
收藏
页码：278 / 286
页数：9
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