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Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids.
Org Lett. 2015 Jun 19; 17(12):3070-3.OL

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang W
†Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
Sun X
†Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
Yu W
†Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
Rai R
†Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
Deschamps JR
‡Naval Research Laboratory, Code 6930, 4555 Overlook Avenue, Washington, D.C. 20375, United States.
Mitchell LA
‡Naval Research Laboratory, Code 6930, 4555 Overlook Avenue, Washington, D.C. 20375, United States.
Jiang C
§Department of Pharmaceutical Engineering, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, China.
MacKerell AD
†Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.
Xue F
†Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Baltimore, Maryland 21201, United States.

MeSH

CatalysisKeto AcidsLactamsMolecular StructurePolycyclic Aromatic HydrocarbonsSpiro Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

26043081

Citation

Yang, Wei, et al. "Facile Synthesis of Spirocyclic Lactams From β-Keto Carboxylic Acids." Organic Letters, vol. 17, no. 12, 2015, pp. 3070-3.
Yang W, Sun X, Yu W, et al. Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids. Org Lett. 2015;17(12):3070-3.
Yang, W., Sun, X., Yu, W., Rai, R., Deschamps, J. R., Mitchell, L. A., Jiang, C., MacKerell, A. D., & Xue, F. (2015). Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids. Organic Letters, 17(12), 3070-3. https://doi.org/10.1021/acs.orglett.5b01350
Yang W, et al. Facile Synthesis of Spirocyclic Lactams From β-Keto Carboxylic Acids. Org Lett. 2015 Jun 19;17(12):3070-3. PubMed PMID: 26043081.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids. AU - Yang,Wei, AU - Sun,Xianyu, AU - Yu,Wenbo, AU - Rai,Rachita, AU - Deschamps,Jeffrey R, AU - Mitchell,Lauren A, AU - Jiang,Chao, AU - MacKerell,Alexander D,Jr AU - Xue,Fengtian, Y1 - 2015/06/04/ PY - 2015/6/5/entrez PY - 2015/6/5/pubmed PY - 2016/5/18/medline SP - 3070 EP - 3 JF - Organic letters JO - Org Lett VL - 17 IS - 12 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26043081/Facile_Synthesis_of_Spirocyclic_Lactams_from_β_Keto_Carboxylic_Acids_ DB - PRIME DP - Unbound Medicine ER -