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Rapid Access to Polyfunctionalized 3,4-Dihydroquinazolinones through a Sequential N-Acyliminium Ion Mannich Reaction Cascade
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.ORCID iD: 0000-0002-9441-3767
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
2015 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 35, 7743-7755 p.Article in journal (Refereed) Published
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Abstract [en]

A microwave-promoted one-pot, three-component sequential cyclization-Mannich reaction of unactivated ketones, o-formyl carbamates and primary amines has been developed. Cyclic N-acyliminium ions are generated in situ from the carbamate and amine starting materials. This metal-free cascade protocol provides rapid access to structurally diverse 3,4-dihydroquinazolinones in good to excellent yields with high regioselectivity for the terminal methyl group, in the case of unsymmetrical methyl alkyl ketones. Key features of the developed protocol include its operational simplicity, ease of product purification, and wide functional group tolerance.

Place, publisher, year, edition, pages
2015. no 35, 7743-7755 p.
Keyword [en]
Multicomponent reactions, Domino reactions, Nitrogen heterocycles, Mannich bases, Regioselectivity
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-268568DOI: 10.1002/ejoc.201501178ISI: 000366426600015OAI: oai:DiVA.org:uu-268568DiVA: diva2:900596
Available from: 2016-02-04 Created: 2015-12-08 Last updated: 2017-11-30Bibliographically approved

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Publisher's full texthttp://dx.doi.org/10.1002/ejoc.201501178

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Sawant, Rajiv T.Stevens, Marc Y.Odell, Luke R.

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