Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines.

A traceless polymer-supported synthesis of 4-benzoylquinazolines was developed using the following commercially available building blocks: Fmoc-α-amino acids, 2-nitrobenzensulfonyl chlorides and α-bromoacetophenones. The acyclic intermediates underwent base-catalyzed rearrangement involving C-C and N-N bond formation followed by ring expansion and yielded resin-bound dihydroquinazoline-2-carboxylic acids. After they were released from the resin by treatment with trifluoroacetic acid, base-mediated decarboxylation produced the target quinazolines in moderate-to-high yields and purities.

Citation

Veronika Fülöpová, Lauren Cziesla, Megan Fleming, Yiwei Lu, Adrienne Voelker, Viktor Krchňák. Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines. ACS combinatorial science. 2015 Aug 10;17(8):470-3

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PMID: 26145229

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