杯芳烃α-酮乙炔：与肼亲核试剂反应的多功能平台。

Muravev Anton A, Solovieva Svetlana E, Galieva Farida B, Bazanova Olga B, Rizvanov Ildar Kh, Ivshin Kamil A, Kataeva Olga N, Matthews Susan E, Antipin Igor S

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS Kazan 420088 Russia

A.M. Butlerov Institute of Chemistry, Kazan Federal University Kazan 420008 Russia.

RSC Adv. 2018 Sep 21;8(57):32765-32769. doi: 10.1039/c8ra06349d. eCollection 2018 Sep 18.

Late stage diversification of calix[4]arenes and thiacalix[4]arenes with heterocycles remains a significant synthetic challenge and hampers further exploitation of the scaffolds. Here we describe the development of a short and facile synthetic route to conformationally diverse novel calix[4]arene and thiacalix[4]arene ynones using a palladium cross coupling approach (5% Pd(ii) + 10% Cu(i)) with benzoyl chloride. Their successful conversion to heterocycles to afford pyrazoles was demonstrated through treatment with hydrazine. Functionalisation is calixarene conformation and linker independent enabling access to a library of structures.

杯[4]芳烃和硫杂杯[4]芳烃与杂环的后期多样化仍然是一个重大的合成挑战，并阻碍了对这些支架的进一步开发。在此，我们描述了一种简短且简便的合成路线，该路线使用钯交叉偶联方法（5% Pd(ii) + 10% Cu(i)）与苯甲酰氯，来合成构象多样的新型杯[4]芳烃和硫杂杯[4]芳烃炔酮。通过用肼处理，证明了它们成功转化为杂环以得到吡唑。官能化与杯芳烃的构象和连接基无关，从而能够获得一系列结构。