Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi-Mumm and regiospecific quinazolinone rearrangements
| Autor: | Ilia A. Guzei, Jennifer E. Golden, Victor A. Jaffett, Alok Nerurkar, Xufeng Cao |
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| Rok vydání: | 2019 |
| Předmět: |
Steric effects
Models Molecular Molecular Structure 010405 organic chemistry Organic Chemistry Amidines Stereoisomerism 010402 general chemistry Crystallography X-Ray 01 natural sciences Biochemistry Combinatorial chemistry Article 0104 chemical sciences Amidine chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Quinazolinone Quinazolinones |
| Zdroj: | Organicbiomolecular chemistry. 17(12) |
| ISSN: | 1477-0539 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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