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
Anichini, B
Goti, A
Brandi, A
Kozhushkov, SI
deMeijere, A
[J]. 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
Attanasi, OA
De Crescentini, L
Favi, G
Filippone, P
Lillini, S
Mantellini, F
Santeusanio, S
[J]. 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
Attanasi, OA
De Crescentini, L
Filippone, P
Mantellini, F
Santeusanio, S
[J]. 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
Attanasi, Orazio A.
Favi, Gianfranco
Filippone, Paolino
Giorgi, Gianluca
Mantellini, Fabio
Moscatelli, Giada
Spinelli, Domenico
[J]. ORGANIC LETTERS, 2008, 10 (10) : 1983 - 1986
[8] Azavinyl azomethine ylides from thermal ring opening of α-aziridinohydrazones:: Unprecedented 1,5-electrocyclization to imidazoles
Attanasi, Orazio A.
Davoli, Paolo
Favi, Gianfranco
Filippone, Paolino
Forni, Arrigo
Moscatelli, Giada
Prati, Fabio
[J]. 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
Attanasi, Orazio A.
Favi, Gianfranco
Filippone, Paolino
Lillini, Samuele
Mantellini, Fabio
Spinelli, Domenico
Stenta, Marco
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (06) : 907 - 915
[10] A Novel and Convenient Protocol for Synthesis of Pyridazines
Attanasi, Orazio A.
Favi, Gianfranco
Filippone, Paolino
Perrulli, Francesca R.
Santeusanio, Stefania
[J]. ORGANIC LETTERS, 2009, 11 (02) : 309 - 312

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