Pavlik, James W.
Pyranopyrazoles 5a-i were obtained in a three/four-step synthesis in which pyrazolin-5-one 1a-b were reacted with unsaturated acyl chlorides such as 2a-d, in the presence of calcium hydroxide or magnesium ethoxide. Compounds 3a-b and 3g were allowed to react with Br2 and then dehydrobrominated with 1,8 diazabicyclo (5.4.0)undec-7- ene to yield the final pyranopyrazole 5a-b and 5g. Compounds 3c-f were first converted to 4c-f by treatment with conc. sulfuric acid and then brominated with Br2 and dehydro- brominated with 1,8-diazabicyclo (5.4.0) undec-7-ene to yield pyranopyrazole 5c-f and 5h-i.
Worcester Polytechnic Institute
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Chemistry and Biochemistry