ArticleOrganic & biomolecular chemistry2019
Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi-Mumm and regiospecific quinazolinone rearrangements.
Article in Organic & biomolecular chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Recent Advances in One-Pot Multicomponent Reactions for the Synthesis of Substituted Quinazolin-4(3Molecules (Basel, Switzerland) · 2025Review
- Efficacy of a brain-penetrant antiviral in lethal Venezuelan and eastern equine encephalitis mouse models.Science translational medicine · 2023Article
- Piperazinobenzodiazepinones: New Encephalitic Alphavirus Inhibitors via Ring Expansion of 2-Dichloromethylquinazolinones.ACS medicinal chemistry letters · 2022Article
- Diastereoselective, Multicomponent Synthesis of Pyrrolopyrazinoquinazolinones via a Tandem Quinazolinone Rearrangement/Intramolecular Ring Closure of Tautomeric (Organic letters · 2021Article
- Construction ofAdvanced synthesis & catalysis · 2021Article
- Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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5 authors.
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Abstract
An efficient four-step, six-transformation protocol was developed to afford bioactive N-alkyl- or N-arylamide (E)-arylamidines featuring strategic amidine C3 modifications which were inaccessible or low yielding by previous methods. This synthetic approach, exemplified with 24 amidines and requiring only a single purification, highlights a multicomponent Ugi-Mumm rearrangement to afford highly diversified quinazolinones which undergo regiospecific rearrangement to afford new amidines. The method extensively broadens the structural scope of this new class of trisubstituted amidines and demonstrates the tolerance of regional C3 amidine steric bulk, visualized with X-ray crystallographic analysis.
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