Kawasaki Taishi, Yamamoto Yoshinori
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan.
J Org Chem. 2002 Jul 26;67(15):5138-41. doi: 10.1021/jo025659x.
Various kinds of 6H-dibenzo[b,d]pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which the ortho-position of aryl group is substituted with enynes or iodine, with acetylenes 2 in the presence of palladium and copper catalysts. The Sonogashira coupling between the aryl 3-bromopropenoates 1a and 1b, bearing enynes at the ortho-position of aryl group, and alkynes 2a-g gave the enyne intermediates 3 in situ, which subsequently underwent the palladium-catalyzed benzannulation reaction to afford the 6H-dibenzo[b,d]pyran-6-ones 5a-g and 6. The Sonogashira coupling between the aryl 3-bromopropenoate 1c, bearing iodine at the ortho-position of aryl group, and diynes 2f and 2h produced the diyne intermediates 13, which underwent the benzannulation reaction to afford the 6H-dibenzo[b,d]pyran-6-ones 14f and 14h.
通过一锅法连续反应，使用芳基3-溴丙烯酸酯1（其中芳基的邻位被烯炔或碘取代）与乙炔2在钯和铜催化剂存在下进行Sonogashira偶联-苯并环化反应，合成了各种6H-二苯并[b,d]吡喃-6-酮4。在芳基邻位带有烯炔的芳基3-溴丙烯酸酯1a和1b与炔烃2a-g之间的Sonogashira偶联原位生成烯炔中间体3，随后该中间体进行钯催化的苯并环化反应，得到6H-二苯并[b,d]吡喃-6-酮5a-g和6。在芳基邻位带有碘的芳基3-溴丙烯酸酯1c与二炔2f和2h之间的Sonogashira偶联产生二炔中间体13，该中间体进行苯并环化反应，得到6H-二苯并[b,d]吡喃-6-酮14f和14h。
