A Traceless Approach for the Parallel Solid-Phase Synthesis of 2-(Arylamino)quinazolinones
- 13 July 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (16) , 5831-5834
- https://doi.org/10.1021/jo020236g
Abstract
A traceless approach for the parallel solid-phase synthesis of 2-arylamino-substituted quinazolinones is described. Acylation of MBHA resin with o-nitrobenzoic acid derivatives, followed by reduction of the nitro group with tin chloride, generated a resin-bound o-anilino derivative. Reaction of resin-bound o-anilino derivative with arylisothiocyanates yielded resin-bound thioureas, which reacted with amines in the present of Mukaiyama's reagent (2-chloro-1-methylpyridinium iodide) to afford resin-bound guanidines. Following intramolecular cyclization of the resin-bound guanidines during cleavage from the resin by HF/anisole (95/5) for 1.5 h at 0 °C, the desired products were obtained in good yield and purity.Keywords
This publication has 33 references indexed in Scilit:
- Substituted Isoquinolines and Quinazolines as Potential Antiinflammatory Agents. Synthesis and Biological Evaluation of Inhibitors of Tumor Necrosis Factor αJournal of Medicinal Chemistry, 1999
- Solid-Phase Synthesis of 3H-Quinazolin-4-ones Based on an Aza Wittig-Mediated annulation StrategySynlett, 1998
- The preparation and sar of 4-(anilino), 4-(phenoxy), and 4-(thiophenoxy)-quinazolines: Inhibitors of p56lck and EGF-R tyrosine kinase activityBioorganic & Medicinal Chemistry Letters, 1997
- An efficient solid phase synthetic route to 1,3-disubstituted 2,4(1H,3H)-Quinazolinediones suitable for combinatorial synthesisBioorganic & Medicinal Chemistry Letters, 1996
- Multiple-Component Condensation Strategies for Combinatorial Library SynthesisAccounts of Chemical Research, 1996
- A Specific Inhibitor of the Epidermal Growth Factor Receptor Tyrosine KinaseScience, 1994
- Synthesis and activity in cognition-related tests of novel 2-benzoylamino-4-oxoquinazolinesBioorganic & Medicinal Chemistry Letters, 1992
- Synthesis and structure-activity relationships of N,N'-di-o-tolylguanidine analogs, high-affinity ligands for the haloperidol-sensitive .sigma. receptorJournal of Medicinal Chemistry, 1990
- Potent inhibition of thymidylate synthase by two series of nonclassical quinazolinesJournal of Medicinal Chemistry, 1990
- Synthesis and histamine H2-antagonist activity of 4-quinazolinone derivatives.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988