Open AccessEffective Synthesis of N ‐Arylformamide from α‐Halo‐ N ‐arylacetamides
Author(s) -
Chiang KunHeng,
Lu ShiHan,
Yen WanPing,
Uramaru Naoto,
Tseng WeiSiou,
Chang TeWei,
Wong Fung Fuh
Publication year - 2016
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.21321
Subject(s) - chemistry , acetamide , formamide , medicinal chemistry , iodoacetamide , organic chemistry , enzyme , cysteine
A convenient synthetic method for N ‐arylformamide derivatives was successfully developed by reacting α‐iodo‐ N ‐arylacetamides with formamide. This method was applicable to α‐iodo‐ N ‐arylacetamide substrates bearing electron‐donating or electron‐withdrawing groups, N ‐(benzo[d][1,3]dioxol‐5‐yl)‐2‐iodoacetamide, 2‐iodo‐ N ‐(pyridin‐2‐yl)acetamide, and 2‐iodo‐ N ‐(naphthalen‐4‐yl)acetamide to give the corresponding N ‐arylformamides in moderate to excellent yields (65–94%). A plausible mechanism was proposed to account for the new transformation.