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Synlett 2001; 2001(3): 0333-0336
DOI: 10.1055/s-2001-11413
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Solid-phase Synthesis of Quinazoline-2,4-diones Using SNAr Reaction

Shingo Makino* , Nobuyasu Suzuki, Eiji Nakanishi, Takashi Tsuji
  • *Pharmaceutical Research Laboratories, Ajinomoto Co., Inc. 1-1. Suzuki-cho., Kawasaki-ku. Kawasaki-shi. 210-8681, Japan; Fax + 81(44)2 10 58 71; E-mail: shingo makino@ajinomoto.com
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Publication Date:
31 December 2001 (online)

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We report an efficient solid-phase synthesis of diverse 1,3N-disubstituted quinazoline-2,4-diones. Since substitutions at the 1N-position of quinazolidine-2,4-diones were introduced by reaction between primary amines and 2-fluoro-5-nitrobenzoyl amides (SNAr reaction), substitutions that cannot be prepared by alkylation or arylation can be easily introduced. In addition, the nitro group of quinazoline-2,4-diones can be repeatedly reduced to provide 3N-amines for quinazoline-2,4-dione syntheses, allowing the synthesis of quinazoline-2,4-dione oligomers and polymers. An oligomer with four quinazoline-2,4-dione units was successfully synthesized.

solid-phase synthesis - quinazoline-2,4-dione - SNAr reaction - polymer