Aziridines versus vinyl carbamates from the direct amination of electron-withdrawing group-substituted trifluoromethyl enoates

被引：35

作者：

Fioravanti, S ^{[1
]}

Colantoni, D ^{[1
]}

Pellacani, L ^{[1
]}

Tardella, PA ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 08期

关键词：

D O I：

10.1021/jo050044w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aza-MIRC (Michael-initiated ring closure) and C-H insertion products were obtained in the reactions of trifluoro-methylated olefins with different nosyloxycarbamates by changing base and solvent. Aza-Michael addition products were not isolated. The presence and the position of the trifluoromethyl group allow control of the outcome of the reactions.

引用

页码：3296 / 3298

页数：3

共 43 条

[1]

[Anonymous], [No title captured], Patent No. 396364

[2]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[3]

Banks R.E., 1994, ORGANOFLUORINE CHEM

[4] DILUTION EFFECTS ON REACTION OF CARBETHOXYNITRENE WITH TRANS-1,2-DIMETHYLCYCLOHEXANE WITH HEXAFLUOROBENZENE AND REACTIVE SOLVENTS [J].

BELLOLI, RC ;

LABAHN, VA .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (13) :1972-1973

[5] Reactivity of stable trifluoroacetaldehyde hemiaminals. I. An unexpected reaction with enolizable carbonyl compounds [J].

Blond, G ;

Billard, T ;

Langlois, BR .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4826-4830

[6]

Cardillo G, 2003, ALDRICHIM ACTA, V36, P39

[7] Aza-Michael addition of nosyloxycarbamates to 2-(trifluoromethyl)acrylates [J].

Colantoni, D ;

Fioravanti, S ;

Pellacani, L ;

Tardella, PA .

ORGANIC LETTERS, 2004, 6 (02) :197-200

[8] Trifluoromethyl-containing 3-alkoxymethyl- and 3-aryloxymethyl-2-pyridinones are potent inhibitors of HIV-1 non-nucleoside reverse transcriptase [J].

Corbett, JW ;

Kresge, KJ ;

Pan, SL ;

Cordova, BC ;

Klabe, RM ;

Rodgers, JD ;

Erickson-Viitanen, SK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) :309-312

[9] Synthesis of enantiomerically pure α-ethyl, α-vinyl and α-ethynyl 3,3,3-trifluoro alaninates [J].

Crucianelli, M ;

De Angelis, F ;

Lazzaro, F ;

Malpezzi, L ;

Volonterio, A ;

Zanda, M .

JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (04) :573-577

[10] Synthesis of N-protected cyano aziridines [J].

Fioravanti, S ;

Morreale, A ;

Pellacani, L ;

Tardella, PA .

SYNLETT, 2004, (06) :1083-1085

← 1 2 3 4 5 →