Oxa-ene reaction of enols of amides with 4-phenyl-1,2,4-triazoline-3,5-dione

被引：10

作者：

Basheer, Ahmad ^{[1
,2
]}

Rappoport, Zvi ^{[1
,2
]}

机构：

[1] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel

[2] Hebrew Univ Jerusalem, Lise Meitner Minerva Ctr Computat Quantum Chem, IL-91904 Jerusalem, Israel

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 01期

关键词：

D O I：

10.1021/jo702083u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The reaction of 16 enols of amides with 4-phenyl-1,2,4-triazoline-1,3-dione gave open chain adducts rather than the [2 + 2] cycloadducts with a hemiaminal moiety, both in solid state and in solution. This assignment is based on X-ray crystallography, H-1 and C-13 NMR data, and IR spectra. The suggested mechanism involves hydroxyl proton loss in a formal oxa-ene reaction. Mechanistic details and a possible alternative are discussed.

引用

收藏

页码：184 / 190

页数：7

相关论文

共 54 条

[31] N-isopropyl enols of carboxylic acid amides [J].

Lei, YX ;

Casarini, D ;

Cerioni, G ;

Rappoport, Z .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2003, 16 (08) :525-545

[32] Stable enols of amides ArNHC(OH)=C(CN)CO2R.: E/Z enols, equilibria with the amides, solvent effects, and hydrogen bonding [J].

Lei, YX ;

Casarini, D ;

Cerioni, G ;

Rappoport, Z .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :947-959

[33] Reactions of enols of amides with diazomethane [J].

Lei, YX ;

Rappoport, Z .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :6971-6978

[34] Enols of amides. the effect of fluorine substituents in the ester groups of dicarboalkoxyanilidomethanes on the enol/amide and E-enol/Z-enol ratios.: A multinuclei NMR study [J].

Lei, YX ;

Cerioni, G ;

Rappoport, Z .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8379-8394

[35] Stable enols of carboxylic esters. The poly(methoxycarbonyl)cyclopentadiene systems [J].

Lei, YX ;

Cerioni, G ;

Rappoport, Z .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) :4028-4038

[36] AZODICARBONYL COMPOUNDS IN HETEROCYCLIC SYNTHESIS [J].

MOODY, CJ .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1982, 30 :1-45

[37] Enols of carboxylic acid amides with β-electron-withdrawing substituents [J].

Mukhopadhyaya, JK ;

Sklenák, S ;

Rappoport, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1325-1336

[38] Cyano-, nitro-, and alkoxycarbonyl-activated observable stable enols of carboxylic acid amides [J].

Mukhopadhyaya, JK ;

Sklenak, S ;

Rappoport, Z .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :6856-6867

[39] DIRECT OBSERVATION OF THE AZIRIDINIUM IMIDE INTERMEDIATES IN THE REACTION OF BIADAMANTYLIDENE WITH TRIAZOLINEDIONES [J].

NELSEN, SF ;

KAPP, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5548-5549

[40] ENE REACTION OF TRIAZOLINEDIONES WITH ALKENES .2. KINETICS AND SUBSTITUENT EFFECTS [J].

OHASHI, S ;

BUTLER, GB .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (17) :3472-3476

← 1 2 3 4 5 6 →