Solid-phase synthesis of 4,8-disubstituted-8,9-dihydropyrazino[2,3-g]quinazolin-7(6H)-ones

✍ Scribed by Yandong Zhang; Chao Yao; Richard A. Houghten; Yongping Yu

• Publisher: Wiley (John Wiley & Sons)
• Year: 2007
• Tongue: English
• Weight: 117 KB
• Volume: 90
• Category: Article
• ISSN: 0006-3525
• DOI: 10.1002/bip.20842

✦ Synopsis

Abstract

An approach for the solid‐phase synthesis of 4,8‐disubstituted‐8,9‐dihydropyrazino[2,3‐g]quinazolin‐7(6__H__)‐ones from 4‐chloro‐7‐fluoro‐6‐nitroquinazoline scaffold is described. A chemoselective reaction of resin‐bound arylamines (3) with 4‐chloro‐7‐fluoro‐6‐nitroquinazoline (8) yielded resin‐bound 4‐arylamino‐7‐fluoro‐6‐nitroquinazolines (4), which were reacted with amino acid methyl esters to afford the corresponding resin‐bound compound (5). Following the reduction of nitro group and intramolecular cyclization of 5, resin‐bound 4,8‐disubstituted‐8,9‐dihydropyrazino[2,3‐g]quinazolin‐7(6__H__)‐one (6) was yielded. The desired products (7) were obtained in good yields and purities after cleavage from the resin. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 90: 439–443, 2008.

This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at [email protected]