Abstract:
Depending on conditions, reaction of 3-amino-4H-chromeno[3,4-d]isoxazol-4-one with benzoyl chloride gives 4-hydroxy- and/or 4-benzoyloxy-3-(5-phenyl-1,2,4-oxadiazol-3-yl)coumarins, which are rearranged into 2-benzamido-4H-chromeno[3,4-d]oxazol-4-one by heating in DMSO.
Citation:
V. Ya. Sosnovskikh, V. S. Moshkin, M. Yu. Kornev, M. I. Kodess, “Reactions of 3-aminoisoxazolo[4,5-c]coumarin with benzoyl chloride: the first example of a preparative 1,2,4-oxadiazole–oxazole rearrangement”, Mendeleev Commun., 21:2 (2011), 110–111
Linking options:
https://www.mathnet.ru/eng/mendc2884
https://www.mathnet.ru/eng/mendc/v21/i2/p110
This publication is cited in the following 6 articles:
Antonio Palumbo Piccionello, Ivana Pibiri, Andrea Pace, Silvestre Buscemi, Nicolò Vivona, Comprehensive Heterocyclic Chemistry IV, 2022, 147
Antonio Palumbo Piccionello, Andrea Pace, Silvestre Buscemi, “Rearrangements of 1,2,4-Oxadiazole: “One Ring to Rule Them All””, Chem Heterocycl Comp, 53:9 (2017), 936
A. V. Galenko, A. F. Khlebnikov, M. S. Novikov, V. V. Pakalnis, N. V. Rostovskii, “Recent advances in isoxazole chemistry”, Russian Chem. Reviews, 84:4 (2015), 335–377
V. Y. Sosnovskikh, V. S. Moshkin, “Novel data for the reaction of 3-cyano-(thio)chromones with N-nucleophiles”, Chem Heterocycl Comp, 48:1 (2012), 139
Zulhusni B. Saad, Shu Xian Chong, Zhi Xiang Wong, Hassan H. Abdallah, Abdulaziz A. Al-Saadi, “Structural properties and vibrational spectra of 2-formyloxazole and its 2-thioformyl and 2-selenoformyl derivatives”, Journal of Molecular Structure, 1006:1-3 (2011), 655
Vyacheslav Ya. Sosnovskikh, Vladimir S. Moshkin, Mikhail Yu. Kornev, Mikhail I. Kodess, “ChemInform Abstract: Reactions of 3‐Aminoisoxazolo[4,5‐c]coumarin with Benzoyl Chloride: The First Example of a Preparative 1,2,4‐Oxadiazole—Oxazole Rearrangement.”, ChemInform, 42:34 (2011)
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