Synthesis of chromeno[3,4-c][1,2]oxazine-N-oxides via formal [4+2] cycloaddition of 3-nitro-2-trihalomethyl-2H-chromenes with cyclohexanone and pinacolone enamines |
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| Authors: | Vladislav Yu Korotaev Alexey Yu Barkov Evgeniya G Matochkina Mikhail I Kodess Vyacheslav Ya Sosnovskikh |
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| Institution: | 1. Department of Chemistry, Institute of Natural Sciences, Ural Federal University, 620000 Ekaterinburg, Russian Federation;2. Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620041 Ekaterinburg, Russian Federation |
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| Abstract: | 3-Nitro-2-trichloro(trifluoro)methyl-2H-chromenes undergo a formal 4+2] cycloaddition reaction to cyclohexanone and pinacolone enamines, producing chromeno3,4-c]1,2]benzoxazin-6-oxides with high diastereoselectivity and in good yields. In addition, some novel 2,3,4-trisubstituted chromanes were obtained. The stereochemistry of the products was established based on a 2D NOESY experiment and an X-ray diffraction study. |
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| Keywords: | 3-Nitro-2-trihalomethyl-2H-chromenes Enamines Cyclic nitronates 2 3 4-Trisubstituted chromanes Stereoselectivity |
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