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.

• This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

Creator

• Martinez, Jessica Alexandra

Publisher

• Worcester Polytechnic Institute

Identifier

• 06C051M

Advisor

• Pavlik, James W.

Year

• 2006

Date created

• 2006-01-01

Resource type

• Major Qualifying Project

Major

• Chemistry

Rights statement

• In Copyright