Synthesis and photochemistry of 3-(o-stilbeneyl)-4-H/Me/Ph-sydnones; intramolecular cyclization to 1,2-benzodiazepines and/or quinolines |
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Authors: | Kristina Butkovi? ?eljko Marini? Marija Šindler-Kulyk |
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Institution: | a Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Maruli?ev trg 19, 10000 Zagreb, Croatia b Center for NMR, Rudjer Boškovi? Institute, Bijeni?ka cesta 54, 10000 Zagreb, Croatia |
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Abstract: | Stilbeneylsydnone derivatives were synthesized by a sequence of reactions in good yields. Irradiation of 3-stilbeneyl-4-methylsydnone 4 gives 1H-1,2-benzodiazepine derivative 7 as the main product along with 2-methylquinoline derivative 20. Irradiation of 3-stilbeneyl-4-phenylsydnone 5 afforded only 1H-1,2-benzodiazepine derivative 8 whereas on irradiation of 4-unsubstituted 3-stilbeneylsydnone 3 no benzodiazepine derivative was detected. An efficient novel photochemical approach to 1H-1,2-benzodiazepines has been found from the new 3-(o-stilbeneyl)-4-substituted-sydnones via intramolecular 1,7-electrocyclization reaction of the photogenerated nitrile imines. |
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Keywords: | Cyclization Benzodiazepines Nitrile imines Stilbenes Sydnones Quinolines |
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