TfOH-mediated [2 + 2 + 2] cycloadditions of ynamides with two discrete nitriles: synthesis of 4-aminopyrimidine derivatives

Abstract

In this study, a concise and atom-economical TfOH-mediated [2 + 2 + 2] cycloaddition of ynamides with two discrete nitriles is developed to synthesize multi-substituted 4-aminopyrimidine.

Synthesis of 3‐Amino‐1‐benzothiophene‐1,1‐diones by Alkyne Directed Hydroarylation and 1/N→3/C‐Sulfonyl Migration

“…13 C NMR [101 MHz, CDCl 3 ]: δ = 14.2, 21.8, 38.5, 61.6, 66.0, 83.5, 128.0, 130.2, 133.0, 145.8, 154.1 ppm. These data were in accordance to those reported in the literature …”

Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N,N-Dimethylaminoethanol as One Carbon Donor

“…14 Besides, the condensation of aldehydes, ketones with NH 4 OAc, 15 or of 1,3-diketones, aldehydes, and NH 4 OAc 16 also afforded pyrimidines. It was also demonstrated that the reaction of alkynes and nitriles in the presence of Lewis acids 17 or a cyclization of ketones with two molecules of nitriles provided the pyrimidine skeleton. 18 Recently, Fan and co-workers have reported a methodology for the synthesis of pyrimidines from amidines and ketones using DMF as one carbon source through C(sp 3 )−H activation mediated by TBHP (tert-butyl hydroperoxide) (Scheme 1a).…”

Recent Advances in the Ring-Forming Reactions of Ynamides

“…图式 70 炔酰胺参与的[3＋2]环加成反应合成氨基噁唑 Scheme 70 Synthesis of aminooxazoles by [3＋2] cycloaddition of ynamides 2019 年, 李清江和王洪根等 [75] [85] 和蔡明中 [86] 等报道了类似的 Au(I)催化炔 酰胺与腈类化合物的[2＋2＋2]环加成反应, 并研究其 机理. 唐宇等 [87]…”