Synthesis of fused heterocycles from 2-aryl-5-(chlorosulfonyl)-1,3-oxazole-4-carboxylates and α-aminoazoles involving the Smiles rearrangement
| Autor: | Maryna Kachaeva, Stepan Pilyo, Sergiy Popilnichenko, Andrii Kornienko, Eduard Rusanov, Volodymyr Prokopenko, Vladimir Zyabrev, Volodymyr S. Brovarets |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: | |
| Zdroj: | Current Chemistry Letters, Vol 7, Iss 4, Pp 101-110 (2018) |
| Druh dokumentu: | article |
| ISSN: | 1927-7296 1927-730X |
| DOI: | 10.5267/j.ccl.2018.9.001 |
| Popis: | Reaction of methyl 2-aryl-5-(chlorosulfonyl)-1,3-oxazole-4-carboxylates with 1H-pyrazol-5-amines and 1H-1,2,4-triazol-5-amines proceeds with the participation of endocyclic aminoazole nitrogen atoms to yield products containing a primary amino group. Being treated by sodium hydride these products undergo a further transformation into the tricyclic compounds. It has been shown that the cyclocondensation pathway includes the Smiles rearrangement with extrusion of SO2 followed by the elimination of MeOH. This reaction sequence is a convenient approach to the synthesis of new annulated [1,3]oxazolo[5,4-d]pyrimidine derivatives. |
| Databáze: | Directory of Open Access Journals |
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