title: Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids.
abstract: A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.
authors.affiliation: †Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
authors.forename: Wei
authors.initials: W
authors.lastname: Yang
authors.affiliation: †Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
authors.forename: Xianyu
authors.initials: X
authors.lastname: Sun
authors.affiliation: †Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
authors.forename: Wenbo
authors.initials: W
authors.lastname: Yu
authors.affiliation: †Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
authors.forename: Rachita
authors.initials: R
authors.lastname: Rai
authors.affiliation: ‡Naval Research Laboratory, Code 6930, 4555 Overlook Avenue, Washington, D.C. 20375, United States.
authors.forename: Jeffrey R
authors.initials: JR
authors.lastname: Deschamps
authors.affiliation: ‡Naval Research Laboratory, Code 6930, 4555 Overlook Avenue, Washington, D.C. 20375, United States.
authors.forename: Lauren A
authors.initials: LA
authors.lastname: Mitchell
authors.affiliation: §Department of Pharmaceutical Engineering, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, China.
authors.forename: Chao
authors.initials: C
authors.lastname: Jiang
authors.affiliation: †Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
authors.forename: Alexander D
authors.initials: AD
authors.lastname: MacKerell
authors.affiliation: †Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
authors.forename: Fengtian
authors.initials: F
authors.lastname: Xue
mesh_terms: D002384:Catalysis; D007651:Keto Acids / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: D007651:Keto Acids; D007769:Lactams; D011084:Polycyclic Aromatic Hydrocarbons; D013141:Spiro Compounds