Synthesis of 1-azadienes by a three-component reaction between isocyanides, esters and 3-hydroxy-2-methyl-4H-pyran-4-one

被引：0

作者：

Souldozi, Ali ^{[1
]}

Pour, Amin Mohammad ^{[1
]}

Karami, Samad ^{[1
]}

机构：

[1] Islamic Azad Univ, Urmia Branch, Dept Chem, Orumiyeh, Iran

来源：

JOURNAL OF CHEMICAL RESEARCH | 2014年 / 03期

关键词：

green synthesis; three-component reaction; 1-azadiens; alkyl isocyanides; acetylenic esters; ONE-POT SYNTHESIS; (N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE; DERIVATIVES;

D O I：

10.3184/174751914X13922166041402

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1:1 reactive intermediate generated by the addition of alkyl isocyanides to dialkyl acetylenedicarboxylates was trapped by 3-hydroxy-2-methyl-4H-pyran-4-one as OH-acid in water to yield highly functionalised 1-azadienes.

引用

页码：178 / 179

页数：2

共 14 条

[1] Highly substituted pyrrolidinones and pyridones by 4-CR/2-CR sequence [J].

Beck, B ;

Picard, A ;

Herdtweck, E ;

Dömling, A .

ORGANIC LETTERS, 2004, 6 (01) :39-42

[2] A convenient preparation of N-acyl-1-aza-1,3-diene from β-formylenamide and its utility in inverse electron demand Diels-Alder reactions [J].

Boruah, RC ;

Ahmed, S ;

Sharma, U ;

Sandhu, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :922-925

[3] N-acylazinium salts: A new source of iminium ions for Ugi-type processes [J].

Diaz, JL ;

Miguel, M ;

Lavilla, R .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3550-3553

[4] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[5] Azadiene Diels-Alder cycloaddition of fulvenes: A facile approach to the [1]pyrindine system [J].

Hong, BC ;

Wu, JL ;

Gupta, AK ;

Hallur, MS ;

Liao, JH .

ORGANIC LETTERS, 2004, 6 (20) :3453-3456

[6] Massive parallel catalyst screening: Toward asymmetric MCRs [J].

Kusebauch, U ;

Beck, B ;

Messer, K ;

Herdtweck, E ;

Domling, A .

ORGANIC LETTERS, 2003, 5 (22) :4021-4024

[7] Studies on isocyanides: synthesis of tetrazolyl-isoindolinones via tandem Ugi four-component condensation/intramolecular amidation [J].

Marcos, Carlos F. ;

Marcaccini, Stefano ;

Menchi, Gloria ;

Pepino, Roberto ;

Torroba, Tomas .

TETRAHEDRON LETTERS, 2008, 49 (01) :149-152

[8] A novel one-pot pseudo-five-component synthesis of 4,5,6,7-tetrahydro-1H-1,4-diazepine-5-carboxamide derivatives [J].

Shaabani, Ahmad ;

Maleki, Ali ;

Mofakham, Hamid ;

Moghimi-Rad, Jafar .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (10) :3925-3927

[9] The reaction of (N-isocyanimino)triphenylphosphorane with dialkyl acetylenedicarboxylates in the presence of 1,3-diphenyl-1,3-propanedione:: a novel three-component reaction for the stereoselective synthesis of dialkyl (Z)-2-(5,7-diphenyl-1,3,4-oxadiazepin-2-yl)-2-butenedioates [J].

Souldozi, Ali ;

Ramazani, Ali ;

Bouslimani, Nouri ;

Welter, Richard .

TETRAHEDRON LETTERS, 2007, 48 (14) :2617-2620

[10] The reaction of (N-isocyanimino)triphenylphosphorane with benzoic acid derivatives:: a novel synthesis of 2-aryl-1,3,4-oxadiazole derivatives [J].

Souldozi, Ali ;

Ramazani, All .

TETRAHEDRON LETTERS, 2007, 48 (09) :1549-1551

← 1 2 →