Novel Synthesis of Aza-phthalimidine Hydroxylactams

Abstract

A novel and convenient synthetic route for preparing aza-phthalimidine hydroxylactams (5a–j) by N-bromosuccinimide (NBS) was developed. This method involved the substitution reactions of substrates (3a–j) with NBS via unstable intermediate bromides (4a–j) rapidly hydrolyzed into hydroxyl products in the course of the workup process.

Keywords:

• N-Bromosuccinimide
• hydroxylactam
• hydroxylation

Notes

^a Isolated yield by method A.

^b Isolated yield by method B.

^c Ref. 8a, mp: 237–239 °C.

^d Ref. 2a, mp: 203–207 °C.