Organic chemistry

Combinatorial chemistry

Ring (chemistry)

Dichloromethane

Medicinal chemistry

Chemistry

Radical cyclization

Solvent

Cyclopropane

Chloroform

Advanced Synthesis & Catalysis

A radical di‐ and trichloromethylation/cyclization of unactivated alkenes was developed with commercially available dichloromethane and chloroform as di‐and trichloromethyl radical sources under metal‐free conditions. Variously substituted di‐ and trichloromethylated pyrrolo‐ and piperidino‐quinazolinones were obtained in 47–94% yields. Additionally, dibromomethylation/cyclization was also achieved under standard conditions when CH 2 Br 2 was utilized. Moreover, the obtained dichloromethylated product can be transformed into 1′ H ‐spiro[cyclopropane‐1,3′‐pyrrolo[2,1‐ b ]quinazolin]‐9′(2′ H )‐one after treating by KOH. magnified image

Radical Polychloromethylation/Cyclization of Unactivated Alkenes: Access to Polychloromethyl‐Substituted Ring‐Fused Quinazolinones