N-heterocyclic carbene-catalyzed atroposelective synthesis of N-N axially chiral 3-amino quinazolinones
| Title | N-heterocyclic carbene-catalyzed atroposelective synthesis of N-N axially chiral 3-amino quinazolinones |
| Publication Type | Journal Article |
| Year of Publication | 2023 |
| Authors | Balanna, K, Barik, S, Barik, S, Shee, S, Manoj, N, Gonnade, RG, Biju, AT |
| Journal | ACS Catalysis |
| Volume | 13 |
| Issue | 13 |
| Pagination | 8752-8759 |
| Date Published | JUN |
| Type of Article | Article |
| ISSN | 2155-5435 |
| Keywords | amino quinazolinones, asymmetriccatalysis, axial chirality, N-heterocycliccarbenes, organocatalysis |
| Abstract | Although the atroposelective synthesisof biaryls and related compoundsbearing axially chiral C-C bonds is well-known, the synthesisof axially chiral C-N bond-containing compounds is relativelyless explored, and the construction of axially chiral N-N bondshas received only scant attention. Demonstrated herein is the N-heterocycliccarbene (NHC)-catalyzed selective amidation reaction, leading to theatroposelective synthesis of N-N axially chiral 3-amino quinazolinones.The NHC-catalyzed reaction of quinazolinones containing a free N-Hmoiety with & alpha;,& beta;-unsaturated aldehydes under oxidativeconditions furnished the atropisomeric quinazolinone derivatives undermild conditions and broad scope. Preliminary studies on experimentaland density functional theory-based N-N rotational barrierdetermination are also presented. |
| DOI | 10.1021/acscatal.3c01709 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 12.9 |