Investigation into the regiochemistry of some isoxazoles derived from 1,3-dipolar cycloaddition of 4-nitrobenzonitrile oxide with some dipolarophiles: A combined theoretical and experimental studies

被引：8
|
作者：
Dorostkar-Ahmadi, N. [1 ]
Bakavoli, M. [1 ]
Moeinpour, F. [2 ]
Davoodnia, A. [1 ]
机构：
[1] Islamic Azad Univ, Fac Sci, Dept Chem, Mashhad Branch, Mashhad, Iran
[2] Islamic Azad Univ, Fac Sci, Dept Chem, Bandar Abbas Branch, Bandar Abbas, Iran
来源：
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY | 2011年 / 79卷 / 05期
关键词：
Regioselectivity; 1,3-dipolar cycloaddition; Nitrile oxide; DFT-based reactivity indexes; B3LYP calculations; QUANTITATIVE CHARACTERIZATION; REGIOSELECTIVITY; ELECTROPHILICITY; NITRILIMINE; REACTIVITY;
D O I：
10.1016/j.saa.2011.04.071
中图分类号：
O433 [光谱学];
学科分类号：
0703 ; 070302 ;
摘要：
Reaction of 4-nitrobenzonitrile oxide(2) which was generated in situ with acrylo nitrile (3), methyl methacrylate (4) and allyl bromide (5) as dipolarphile afforded the new 7a, 8a and 9a compounds respectively. Reactivity and regiochemistry of these reactions were investigated using activation energy calculations and density functional theory (DFT)-based reactivity indexes. The theoretical (CNMR)-C-13 chemical shifts of the cycloadducts which were obtained by CIAO method were comparable with the observed values. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码：1375 / 1380
页数：6
相关论文
共 50 条
  • [21] STUDIES ON HETEROAROMATICITY .16. FURTHER STUDIES ON THERMAL 1,3-DIPOLAR CYCLOADDITION REACTIONS OF SOME AROMATIC HYDROXAMOYL CHLORIDES
    SASAKI, T
    YOSHIOKA, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1968, 41 (09) : 2206 - +
  • [22] Stereochemistry of 1,3-dipolar cycloaddition reaction of azomethine ylides derived from N-alkyl-N-(4-toluenesulphonyl) carbamoylmethyl phenanthridinium with olefinic dipolarophiles
    Trávnícek, M
    Potácek, M
    Mannschreck, A
    HETEROCYCLIC COMMUNICATIONS, 2001, 7 (03) : 213 - 222
  • [23] Intramolecular approach to some new D-ring-fused steroidal isoxazolidines by 1,3-dipolar cycloaddition: synthesis, theoretical and in vitro pharmacological studies
    Frank, Eva
    Mucsi, Zoltan
    Szecsi, Mihaly
    Zupko, Istvan
    Woelfling, Janos
    Schneider, Gyula
    NEW JOURNAL OF CHEMISTRY, 2010, 34 (11) : 2671 - 2681
  • [24] THE STUDIES OF 1,3-DIPOLAR CYCLOADDITION OF DIAZOALKANES TO ISOPROPENYLPHOSPHONATES AND SOME PHYSICOCHEMICAL PROPERTIES OF ORGANO-PHOSPHORUS COMPOUNDS OF THE CYCLOPROPANE SERIES
    GAREEV, RD
    CHERNOVA, AV
    ISHMAEVA, EA
    BERDNIKOV, EA
    SHAGIDULLIN, RR
    STRELKOVA, EN
    DOROZHKINA, GM
    PATSANOVSKII, II
    PUDOVIK, AN
    ZHURNAL OBSHCHEI KHIMII, 1982, 52 (11): : 2444 - 2458
  • [25] STUDIES ON REACTIONS OF HETEROCYCLIC-COMPOUNDS .14. 1,3-DIPOLAR CYCLOADDITION OF SOME ISOQUINOLINIUM YLIDES WITH METHYL PROPIOLATE
    KOBAYASHI, Y
    KUMADAKI, I
    SEKINE, Y
    NAITO, Y
    KUTSUMA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1975, 23 (03) : 566 - 568
  • [26] MASS-SPECTRA OF SOME 3,5-DIARYL-4-NITROISOXAZOLES - EVIDENCE FOR A RETRO 1,3-DIPOLAR CYCLOADDITION
    TUAILLON, J
    VEBREL, J
    LAUDE, B
    GUENOT, P
    ORGANIC MASS SPECTROMETRY, 1987, 22 (08): : 550 - 552
  • [27] Theoretical studies on the stereochemical course of 1,3-dipolar cycloaddition of azomethine ylides derived from indol-2,3-dione and thiazolidine-4-carboxylic acid
    Pardasani, RT
    Pardasani, P
    Yadav, SK
    Bharatam, PV
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (04) : 557 - 563
  • [28] 1,3-dipolar cycloaddition of 1,2-O-isopropylidene-α-D-xylopentadialdo-1,4-furanosenitrile oxide to some alkenes
    Fascio, ML
    Montesano, VJ
    D'Accorso, NB
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (01) : 103 - 107
  • [29] Theoretical and synthetic approach to novel spiroheterocycles derived from isatin derivatives and L-proline via 1,3-dipolar cycloaddition
    Pardasani, RT
    Pardasani, P
    Chaturvedi, V
    Yadav, SK
    Saxena, A
    Sharma, I
    HETEROATOM CHEMISTRY, 2003, 14 (01) : 36 - 41
  • [30] Stereoselective 1,3-dipolar cycloadditions of a chiral nitrone derived from erythrulose.: An experimental and DFT theoretical study
    Carda, M
    Portolés, R
    Murga, J
    Uriel, S
    Marco, JA
    Domingo, LR
    Zaragozá, RJ
    Röper, H
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21): : 7000 - 7009
12345