Photochemical and thermal intramolecular 1,3-dipolar cycloaddition reactions of new o-stilbene-methylene-3-sydnones and their synthesis

被引：18

作者：

Butkovic, Kristina ^{[1
]}

Marinic, Zeljko ^{[2
]}

Molcanov, Kresimir ^{[3
]}

Kojic-Prodic, Biserka ^{[3
]}

Sindler-Kulyk, Marija ^{[1
]}

机构：

[1] Univ Zagreb, Fac Chem Engn & Technol, Dept Organ Chem, Zagreb 10000, Croatia

[2] Rudjer Boskovic Inst, Ctr NMR, Zagreb 10000, Croatia

[3] Rudjer Boskovic Inst, Dept Phys Chem, Lab Chem & Biol Crystallog, Zagreb 10000, Croatia

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 7卷

关键词：

3+2] cycloaddition; isoindoles; nitrile imines; pyrazoles; sydnones; MESOIONIC COMPOUNDS; 3,4-DIARYLSYDNONES; PHOTOREACTIONS; HETEROCYCLES; INHIBITORS; SYDNONES; SYSTEMS; C-13;

D O I：

10.3762/bjoc.7.196

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New trans- and cis-o-stilbene-methylene-sydnones 3a, b were synthesized by transforming the trans- and cis-o-aminomethyl-stilbene derivative, obtained by reduction of corresponding o-cyano derivatives, into glycine ester derivatives (43 and 31% yield) followed by hydrolysis (90 and 96% yield), nitrosation and ring closure with acetic acid anhydride (30 and 40% yield). The products were submitted to photochemical and thermal intramolecular [3 + 2] cycloadditions to afford diverse heteropolycyclic compounds. Photochemical reactions afforded cis-3-(4-methylphenyl)-3a,8-dihydro-3H-pyrazolo[5,1-a]isoindole (11, 12.5% yield) and trans-3-(4-methylphenyl)-3a,8-dihydro-3H-pyrazolo[5,1-a]isoindole (12, 5% yield). Thermal reactions afforded 3-(4-methylphenyl)-3,3a,8,8a-tetrahydroindeno[2,1-c]pyrazole (14, 50% yield) and 11-(4-methylphenyl)-9,10-diazatricyclo[7.2.1.0(2,7)]dodeca-2,4,6,10-tetraene (15, 22% yield).

引用

页码：1663 / 1670

页数：8

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