1447798-29-9Relevant academic research and scientific papers
Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins
Yoshioka, Eito,Kohtani, Shigeru,Miyabe, Hideto
, p. 863 - 880 (2014)
The domino three-component coupling reaction of arynes with DMF and active methylenes or methines was studied as a highly efficient method for preparing heterocycles. Coumarin derivative 5 was formed when diethyl malonate (2) or a-bromomalonate (3) were used as a C2-unit. In contrast, dihydrobenzofurans 7a and 7b were obtained by using a-chloroenolates generated from a-chloromalonates 4a and 4b and Et2Zn. The benzofuran 15a could be obtained by using ethyl iodoacetate (14) as a C1-unit. The one-pot conversion of dihydrobenzofurans 7a, 7b and 8a into benzofurans 15a and 15b was also studied. The direct synthesis of benzofuran 15b was achieved by using the active methine 18 having ketone and ester groups.
Straightforward synthesis of dihydrobenzofurans and benzofurans from arynes
Yoshioka, Eito,Tanaka, Hidekazu,Kohtani, Shigeru,Miyabe, Hideto
supporting information, p. 3938 - 3941 (2013/09/02)
Synthesis of dihydrobenzofurans was achieved by a route involving the insertion of arynes into formamides followed by trapping with zinc enolates of α-chlorinated methines. Benzofurans were generated from dihydrobenzofurans having a ketone group via the addition of an ethyl anion, the retro-aldol type reaction, and the elimination of an amino group.
