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

被引：9
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.
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收藏
页码：184 / 190
页数：7
相关论文
共 54 条
  • [1] ON THE MECHANISM OF THE CYCLOADDITION OF 1,2,4-TRIAZOLINE-3,5-DIONES WITH BICYCLOALKENES LEADING TO REARRANGED URAZOLES
    ADAM, W
    CARBALLEIRA, N
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) : 2874 - 2882
  • [2] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS
    ALLEN, FH
    KENNARD, O
    WATSON, DG
    BRAMMER, L
    ORPEN, AG
    TAYLOR, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12): : S1 - S19
  • [3] Enols of amides activated by the 2,2,2-trichloroethoxycarbonyl group
    Basheer, A
    Rappoport, Z
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) : 1151 - 1160
  • [4] BASHEER A, 2004, 69 M ISR CHEM SOC TE
  • [5] Enols of substituted cyanomalonamides
    Basheer, Ahmad
    Yamataka, Hiroshi
    Ammal, Salai Cheettu
    Rappoport, Zvi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) : 5297 - 5312
  • [6] Billard T, 2001, EUR J ORG CHEM, V2001, P1467
  • [7] SUBSTITUENT AND SOLVENT EFFECTS ON DIELS-ALDER REACTIONS OF TRIAZOLINEDIONES
    BURRAGE, ME
    COOKSON, RC
    GUPTE, SS
    STEVENS, DR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (12): : 1325 - 1334
  • [8] CARRUTHERS W, 1990, CYCLOADDITION REACTI, P353
  • [9] REACTION OF TRIAZOLINEDIONES WITH ACETYLENES - ELECTROPHILIC ADDITION
    CHENG, CC
    GREENE, FD
    BLOUNT, JF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) : 2917 - 2922
  • [10] REACTION OF ELECTROPHILES WITH UNSATURATED SYSTEMS - TRIAZOLINEDIONE-OLEFIN REACTIONS
    CHENG, CC
    SEYMOUR, CA
    PETTI, MA
    GREENE, FD
    BLOUNT, JF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) : 2910 - 2916
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