tailieunhanh - Synthesis of fused heterocycles from 2-aryl-5-(chlorosulfonyl)-1,3-oxazole-4-carboxylates and α-aminoazoles involving the Smiles rearrangement

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. | Synthesis of fused heterocycles from 2-aryl-5- chlorosulfonyl -1 3-oxazole-4-carboxylates and α-aminoazoles involving the Smiles rearrangement Current Chemistry Letters 7 2018 101 110 Contents lists available at GrowingScience Current Chemistry Letters homepage Synthesis of fused heterocycles from 2-aryl-5- chlorosulfonyl -1 3-oxazole-4- carboxylates and α-aminoazoles involving the Smiles rearrangement Maryna Kachaevaa Stepan Pilyoa Sergiy Popilnichenkoa Andrii Kornienkoa Eduard Rusanovb Volodymyr Prokopenkoa Vladimir Zyabrev a and Volodymyr S. Brovaretsa a Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 1 Murmanska St. Kyiv 02094 Ukraine b Institute of Organic Chemistry of the National Academy of Sciences of Ukraine 5 Murmanska St. Kyiv 02660 Ukraine CHRONICLE ABSTRACT Article history Reaction of methyl 2-aryl-5- chlorosulfonyl -1 3-oxazole-4-carboxylates with 1H-pyrazol-5- Received June 13 2018 amines and 1H-1 2 4-triazol-5-amines proceeds with the participation of endocyclic Received in revised form aminoazole nitrogen atoms to yield products containing a primary amino group. Being treated July 20 2018 by sodium hydride these products undergo a further transformation into the tricyclic Accepted September 2 2018 compounds. It has been shown that the cyclocondensation pathway includes the Smiles Available online rearrangement with extrusion of SO2 followed by the elimination of MeOH. This reaction August 2 2018 sequence is a convenient approach to the synthesis of new annulated 1 3 oxazolo 5 4- Keywords d pyrimidine derivatives. 1 3-Oxazole-5-sulfonyl chloride Aminoazole Smiles rearrangement 1 3 Oxazolo 5 4-d pyrimidine 2018 by the authors licensee Growing Science Canada. 1. Introduction Among a variety of pharmaceutically promising amides of azolesulfonic acids oxazolesulfonyl amides seem to us particularly interesting. These species have the weakly aromatic oxazole ring capable to .