| Autor: |
Kuruva Balanna, Soumen Barik, Shilpa Barik, Sayan Shee, Niket Manoj, Rajesh Gonnade, Akkattu Biju |
| Rok vydání: |
2023 |
| DOI: |
10.26434/chemrxiv-2023-7zxsn |
| Popis: |
Although the atroposelective synthesis of biaryls and related compounds bearing axially chiral C-C bonds are well-known, the synthesis of axially chiral C-N bond-containing compounds are relatively less explored, and the construction of axially chiral N-N bonds has received only scant attention. Demonstrated herein is the N-heterocyclic carbene (NHC)-catalyzed selective amidation reaction leading to the atroposelective synthesis of N-N axially chiral 3-amino quinazolinones. The NHC-catalyzed reaction of quinazolinones containing a free N-H moiety with -unsaturated aldehydes under oxidative conditions furnished the atropisomeric quinazolinone derivatives under mild conditions and broad scope. Preliminary studies on experimental and DFT-based N-N rotational barrier determination is also presented. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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