∥Academy of Scientific and Innovative Research, New Delhi 110001, India.
§X-ray Crystallography Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
Org Lett. 2015 May 1;17(9):2226-9. doi: 10.1021/acs.orglett.5b00832. Epub 2015 Apr 15.
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C-C bond migration.
我们在此描述了一种使用 TsN3 作为氨基替代物，通过银催化将 1-(2-氨基苯基)-丙炔醇转化为 4-取代的 3-对甲苯磺酰氨基喹啉的方法。控制反应揭示了该途径由 Ag(I)催化的 5-endo-dig 环化、无催化剂的（2 + 3）环加成和通过氮逐出的环扩张重排组成。作为支持性研究，我们表明在类似条件下，环状烯胺通过 C-C 键迁移生成脒。
