Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine-Azoene Annulation

被引：76

作者：

Attanasi, Orazio A. ^{[1
]}

Favi, Gianfranco ^{[1
]}

Mantellini, Fabio ^{[1
]}

Moscatelli, Giada ^{[1
]}

Santeusanio, Stefania ^{[1
]}

机构：

[1] Univ Urbino Carlo Bo, Ist Chim Organ, I-61029 Urbino, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 08期

关键词：

C BOND FORMATION; ONE-POT; POLYSUBSTITUTED PYRROLES; 1,3-DICARBONYL COMPOUNDS; MULTICOMPONENT REACTIONS; REGIOSELECTIVE SYNTHESIS; SUBSTITUTED PYRROLES; BIOLOGICAL-ACTIVITY; EFFICIENT SYNTHESIS; GENERAL-SYNTHESIS;

D O I：

10.1021/jo200287k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient synthesis of polysubstituted pyrroles by a sequential one-pot three-component reaction between primary aliphatic amines, active methylene compounds, and 1,2-diaza-1,3-dienes (DDs) is reported. The reactions were performed without catalyst and under solvent-free conditions with complete control of pathway selectivity. Notably, the ready availability of the starting materials and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to unknown polysubstituted pyrroles.

引用

页码：2860 / 2866

页数：7

共 89 条

[1] Two Titanium-Catalyzed Reaction Sequences for Syntheses of Pyrroles from (E/Z)-Chloroenynes or α-Haloalkynols [J].

Ackermann, Lutz ;

Sandmann, Rene ;

Kaspar, Ludwig T. .

ORGANIC LETTERS, 2009, 11 (09) :2031-2034

[2] Solvent-free synthesis of penta-substituted pyrroles: one-pot reaction of amine, alkyl acetoacetate, and furnaryl chloride [J].

Alizadeh, Abdolah ;

Babaki, Mohadese ;

Zohreh, Nasrin .

TETRAHEDRON, 2009, 65 (08) :1704-1707

[3]

[Anonymous], HOUBEN WEYL METHODS

[4] Cascading pericyclic reactions: building complex carbon frameworks for natural product synthesis [J].

Arns, Steve ;

Barriault, Louis .

CHEMICAL COMMUNICATIONS, 2007, (22) :2211-2221

[5] Unexpected behavior of the reaction between 1,2-diaza-1,3-butadienes and 3-dimethylaminopropenoates: A useful entry to new pyrrolines, pyrroles, and oxazolines [J].

Attanasi, OA ;

Favi, G ;

Filippone, P ;

Golobic, A ;

Stanovnik, B ;

Svete, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4307-4313

[6] Regio- and stereoselective one-pot synthesis of unknown oxazoline-fused pyridazines by 'Michael addition-pyridazine cyclization-oxazoline cyclization' cascade reactions of 4-chloro-1,2-diaza-1,3-butadienes with 3-dimethylaminopropenoates [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Filippone, Paolino ;

Golobic, Amalija ;

Perrulli, Francesca R. ;

Stanovnik, Branko ;

Svete, Jurij .

SYNLETT, 2007, (19) :2971-2974

[7] Copper(II)/Copper(I)-Catalyzed Aza-Michael Addition/Click Reaction of in Situ Generated α-Azidohydrazones: Synthesis of Novel Pyrazolone-Triazole Framework [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Filippone, Paolino ;

Mantellini, Fabio ;

Moscatelli, Giada ;

Perrulli, Francesca R. .

ORGANIC LETTERS, 2010, 12 (03) :468-471

[8] Cultivating the Passion to Build Heterocycles from 1,2-Diaza-1,3-dienes: the Force of Imagination [J].

Attanasi, Orazio A. ;

De Crescentini, Lucia ;

Favi, Gianfranco ;

Filippone, Paolino ;

Mantellini, Fabio ;

Perrulli, Francesca R. ;

Santeusanio, Stefania .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) :3109-3127

[9] α-Aminoester-Derived Imidazoles by 1,5-Electrocyclization of Azavinyl Azomethine Ylides [J].

Attanasi, Orazio A. ;

Caselli, Emilia ;

Davoli, Paolo ;

Favi, Gianfranco ;

Mantellini, Fabio ;

Ori, Claudia ;

Prati, Fabio .

ORGANIC LETTERS, 2009, 11 (13) :2840-2843

[10] An Efficient One-Pot, Three-Component Synthesis of 5-Hydrazinoalkylidene Rhodanines from 1,2-Diaza-1,3-dienes [J].

Attanasi, Orazio A. ;

De Crescentini, Lucia ;

Favi, Gianfranco ;

Filippone, Paolino ;

Giorgi, Gianluca ;

Mantellini, Fabio ;

Moscatelli, Giada ;

Behalo, Mohamed S. .

ORGANIC LETTERS, 2009, 11 (11) :2265-2268

← 1 2 3 4 5 6 7 8 9 →