School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India.
Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh 495009, India.
J Org Chem. 2020 Jun 19;85(12):7772-7780. doi: 10.1021/acs.joc.0c00279. Epub 2020 Jun 1.
The aza-Diels-Alder reaction of various alkenes and formed 1-aza-1,3-dienes from the reaction of furan/pyrrole/thiophene and PhINTs for the regioselective synthesis of tetrahydropyridine (THP) derivatives was realized. The reaction was catalyzed by TpCu as a catalyst under very mild reaction conditions. Structurally different alkenes, along with an alkyne, have been utilized as dienophiles to afford a wide range of different THP derivatives up to 70% yield. The potential application of the envisaged method was also investigated by a gram-scale synthesis.
通过呋喃/吡咯/噻吩与 PhINTs 的反应，各种烯烃与形成 1-氮杂-1,3-二烯的氮杂-Diels-Alder 反应实现了四氢吡啶（THP）衍生物的区域选择性合成。该反应在 TpCu 作为催化剂的非常温和的反应条件下催化进行。结构不同的烯烃，以及炔烃，都被用作亲二烯体，以高达 70%的收率提供了广泛的不同的 THP 衍生物。还通过克级合成研究了预期方法的潜在应用。
