Lewis acid-promoted cyclizations of o-alkyloxyphenyl-substituted ynamides to construct 2-amidobenzofurans

Abstract

Lewis acid-promoted cyclizations of o-alkyloxyphenyl-substituted ynamides are described for the general construction of medicinally relevant 2-amidobenzofurans. A diverse array of 3-acyl-2-amidobenzofurans could be effectively constructed via a SnCl4-promoted intermolecular cyclization....

TMSOTf-Catalyzed Reactions of N-Arylynamides with Sulfilimines To Construct 2-Aminoindoles and α-Arylated Amidines

“…Therefore, the steric hindrance of substituents on the acetylenic moiety has a significant effect on the results. However, 2-aminoindole 3ff was not observed for the o -methoxyphenyl-terminated ynamide 1ff , while intramolecular cyclization product 2-amidobenzofuran 4 was isolated in 56% yield. , It is worth mentioning that the heteroaromatic terminated ynamide 1gg was also tolerated leading to the corresponding 2-aminoindole 3gg in 28% yield with most of ynamide 1gg decomposed. Then variations in the protecting group of sulfilimines were examined.…”

Optimization of the synthesis of BET BD2 selective inhibitor XY153

“…With the optimized conditions of step a and step b in hand, we began screening the conditions for step c. A preliminary screening was conducted to investigate the reaction conditions of cyclization step mentioned in the literature [17–21] . However, product 1 was not detected under most of the tested reaction conditions.…”

Catalytic intermolecular hydrofunctionalizations of ynamides

“…[1][2][3][4][5] Because of their unique structural characteristics and potential coordination ability, ynamides have now emerged as versatile building blocks in organic synthesis and a variety of intriguing reactivities have been disclosed. [6][7][8][9][10] Some special topics such as intra- [11][12][13][14][15][16] and inter-molecular annulations, [17][18][19][20][21][22] radical reactions, 23,24 and asymmetric transformations 25,26 have been carefully reviewed in the last few years.…”