Tandem Reductive Alkylation−Cyclization for the Preparation of Unsymmetrical 1,4-Disubstituted 2,3-Diketopiperazines
✍ Scribed by Dinsmore, Christopher J.; Bergman, Jeffrey M.
- Book ID
- 126093435
- Publisher
- American Chemical Society
- Year
- 1998
- Tongue
- English
- Weight
- 72 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0022-3263
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Herein we report the efficient syntheses of 1,4-disubstituted-2,3-diketopiperazines and 1,4,5-trisubstituted-2,3-diketopiperazines, which feature a tandem reductive amination and acylation. Aliphatic and aromatic primary amines serve as viable nucleophiles under the mild reaction conditions.
## Abstract Synthesis of 1,2‐disubstituted‐3‐hydroxy‐4(1__H__)‐quinolinones by the cyclization of __N__‐substituted phenacyl or acetonyl anthranilates is described. Two methods were employed for cyclization of anthranilates. Heating in polyphosphoric acid has a wide scope of applicability. The ther