Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes

被引：14

作者：

Attanas, Orazio A. ^{[1
]}

Favi, Gianfranco ^{[1
]}

Giorgi, Gianluca ^{[2
]}

Mantellini, Fabio ^{[1
]}

Karapetyan, Vahuni ^{[3
]}

Langer, Peter ^{[3
,4
]}

机构：

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

[2] Univ Siena, Ctr Interdipartimentale Anal & Determinaz Struttu, I-53100 Siena, Italy

[3] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[4] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

TETRAHEDRON | 2009年 / 65卷 / 28期

关键词：

REVERSE-TRANSCRIPTASE INHIBITORS; HOMOLYTIC AROMATIC-SUBSTITUTION; 1,3-BIS(SILYL ENOL ETHERS); OMEGA-ALKYNYL ACETALS; ORGANIC-SYNTHESIS; BUILDING-BLOCKS; BIOLOGICAL EVALUATIONS; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; GEMINAL ACYLATION;

D O I：

10.1016/j.tet.2009.04.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unknown spiro-cyclopropanated 1-aminopyrrol-2-ones are regioselectively prepared in high yields by Bi(OTf)(3)-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes at room temperature. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5456 / 5461

页数：6

共 89 条

[1] 1,3-Dipolar cycloadditions to methylenespiro[2.2]pentane: A complementary access to spiro cyclopropanated azaheterocycles [J].

Anichini, B ;

Goti, A ;

Brandi, A ;

Kozhushkov, SI ;

deMeijere, A .

CHEMICAL COMMUNICATIONS, 1997, (03) :261-262

[2]

[Anonymous], 1990, CHALLENGES SYNTHETIC

[3]

ATTANASI O, 1984, SYNTHESIS-STUTTGART, P671

[4]

ATTANASI O, 1984, SYNTHESIS-STUTTGART, P873

[5] Efficient synthesis and environmentally friendly reactions of PEG-supported 1,2-diaza-1,3-butadiene [J].

Attanasi, OA ;

De Crescentini, L ;

Favi, G ;

Filippone, P ;

Lillini, S ;

Mantellini, F ;

Santeusanio, S .

ORGANIC LETTERS, 2005, 7 (12) :2469-2471

[6] 1,2-Diaza-1,3-butadienes: just a nice class of compounds, or powerful tools in organic chemistry? Reviewing an experience [J].

Attanasi, OA ;

De Crescentini, L ;

Filippone, P ;

Mantellini, F ;

Santeusanio, S .

ARKIVOC, 2002, :274-292

[7] Flexible protocol for the chemo- and regioselective building of pyrroles and pyrazoles by reactions of Danishefsky's dienes with 1,2-diaza-1,3-butadienes [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Filippone, Paolino ;

Giorgi, Gianluca ;

Mantellini, Fabio ;

Moscatelli, Giada ;

Spinelli, Domenico .

ORGANIC LETTERS, 2008, 10 (10) :1983-1986

[8] Azavinyl azomethine ylides from thermal ring opening of α-aziridinohydrazones:: Unprecedented 1,5-electrocyclization to imidazoles [J].

Attanasi, Orazio A. ;

Davoli, Paolo ;

Favi, Gianfranco ;

Filippone, Paolino ;

Forni, Arrigo ;

Moscatelli, Giada ;

Prati, Fabio .

ORGANIC LETTERS, 2007, 9 (17) :3461-3464

[9] Improved synthesis of pyrroles and indoles via lewis acid-catalyzed Mukaiyama-Michael-type addition/heterocyclization of enolsilyl derivatives on 1,2-diaza-1,3-butadienes. Role of the catalyst in the reaction mechanism [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Filippone, Paolino ;

Lillini, Samuele ;

Mantellini, Fabio ;

Spinelli, Domenico ;

Stenta, Marco .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (06) :907-915

[10] A Novel and Convenient Protocol for Synthesis of Pyridazines [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Filippone, Paolino ;

Perrulli, Francesca R. ;

Santeusanio, Stefania .

ORGANIC LETTERS, 2009, 11 (02) :309-312

← 1 2 3 4 5 6 7 8 9 →