Efficient Synthesis of 1‐Arylquinoxalin‐2(1H)‐ones via Cyclocondensation of N‐Aryl‐Substituted 2‐Nitrosoanilines with Functionalized Alkyl Acetates |
| |
Authors: | Zbigniew Wróbel Karolina Stachowska Andrzej Kwast Izabela Turska |
| |
Institution: | 1. Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44, PL‐01‐224 Warszawa, (phone: +48?22?6328395;2. fax: +48?22?6326681) |
| |
Abstract: | N‐Aryl‐substituted 2‐nitrosoanilines (=2‐nitrosobenzenamines) 1 , readily available by nucleophilic substitution of the ortho‐H‐atom in nitroarenes with arenamines, react with 2‐substituted acetic acid esters in the presence of a weak base giving 1‐arylquinoxalin‐2(1H)‐ones (Scheme 2). This cyclocondensation allows for the synthesis of compounds 2 – 4 , unsubstituted at C(3) or substituted by alkyl, aryl, ester, amide, and keto groups, in good to excellent yields (Tables 1–4). |
| |
Keywords: | Quinoxalin‐2(1H)‐ones Cyclocondensation Acylation |
|
|