Expeditious Routes to Polycyclic Molecular Frameworks via One-Pot, Two-Step Ugi Ring-Closing Sequences

Zhigang Xu; Fabio De Moliner; Alexandra P. Cappelli; Muhammed Ayaz; Christopher Hulme

doi:10.1055/s-0033-1340219

Synlett, Table of Contents

Synlett 2014; 25(2): 225-228
DOI: 10.1055/s-0033-1340219

letter

Expeditious Routes to Polycyclic Molecular Frameworks via One-Pot, Two-Step Ugi Ring-Closing Sequences

Zhigang Xu

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

,

Fabio De Moliner

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

,

Alexandra P. Cappelli

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

,

Muhammed Ayaz

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

,

Christopher Hulme*

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

^bDepartment of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721, USA

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Abstract

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Abstract

A very general and robust multicomponent-reaction protocol involving an Ugi condensation between ethyl glyoxylate, isonitriles, N-Boc-α-amino acids, and mono-N-Boc-protected diamines followed by a series of acid-promoted cyclization steps in a one-pot fashion is reported. This process allows for the assembly of complex polycyclic structures by means of just two simple synthetic operations and a single chromatographic purification in high overall yields. Of note, the first scaffolds derived from a highly selective sequence of ring-closing events involving three internal amino nucleophiles is reported.

Key words

multicomponent reaction - nucleophilic attack - heterocycles - isonitriles - one-pot process

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References

References and Notes

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