Journal ArticleDOI
Formation of ω-(4-oxo-1,4-dihydropyridin-2-yl)alkanamides in the Beckmann rearrangement of spiro-fused cycloalkanone oximes
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In this paper, cycloalkanone oximes were spirofused to 4-oxo-6-methyl-1,2,3,4-tetrahydropyridine fragment through the α-carbon atom and C2, respectively, on heating in polyphosphoric acid.Abstract:
ω-(4-Oxo-1,4-dihydropyridin-2-yl)alkanamides were obtained from cycloalkanone oximes spirofused to 4-oxo-6-methyl-1,2,3,4-tetrahydropyridine fragment through the α-carbon atom and C2, respectively, on heating in polyphosphoric acid. The resulting amides were converted to the corresponding acids and methyl esters. Methylation of 5-(6-methyl-4-oxo-1,4-dihydropyridin-2-yl)pentanamide with diazomethane gave 4-methoxypyridine derivative as the major product and a small amount of N-methyl derivative, 5-(1,6-di-methyl- 4-oxo-1,4-dihydropyridin-2-yl)pentanamide.read more
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Journal ArticleDOI
Comprehensive Heterocyclic Chemistry II: A Review of the Literature 1982−1995. 12 Volume Set Editors-in-chief: Alan R. Katritzky, Charles W. Rees, and Eric, F. V. Scriven. Elsevier (Pergamon): Oxford. 1997. 11 856 pp. $6345.00. ISBN 0-08-042072-9.
Reference EntryDOI
The Beckmann Reactions: Rearrangements, Elimination–Additions, Fragmentations, and Rearrangement–Cyclizations
TL;DR: The photochemical Beckmann rearrangement cyclization was first observed by De Mayo in 1963 and discussed in a review several years ago as mentioned in this paper, but it has not been exploited extensively until the 1960s.
Journal ArticleDOI
Synthesis and antibacterial activity of a novel series of acylides: 3-O-(3-pyridyl)acetylerythromycin A derivatives
Tetsuya Tanikawa,Toshifumi Asaka,Masato Kashimura,Keiko Suzuki,Hiroyuki Sugiyama,Masakazu Sato,Kazuya Kameo,Shigeo Morimoto,Atsushi Nishida +8 more
TL;DR: A novel series of acylides, 3-O-(aryl)acetylerythromycin A derivatives, showed potent antibacterial activity against not only Gram-positive pathogens, including inducibly macrolide-lincosamide-streptogramin B (MLS(B))-resistant and efflux-resistant strains, but also Gram-negative pathogens, such as H. influenzae.
Journal ArticleDOI
Design, synthesis, and biological evaluation of 14-heteroaromatic-substituted naltrexone derivatives: pharmacological profile switch from mu opioid receptor selectivity to mu/kappa opioid receptor dual selectivity.
Yunyun Yuan,Saheem A. Zaidi,Orgil Elbegdorj,Lindsey C. Aschenbach,Guo Li,David Stevens,Krista L. Scoggins,William L. Dewey,Dana E. Selley,Yan Zhang +9 more
TL;DR: Ligand 10 may serve as a novel lead compound to develop MOR/KOR dual-selective ligands, which might possess unique therapeutic value for opioid addiction treatment.
Journal ArticleDOI
Synthese der macrocyclischen Spermidin-Alkaloide Oncinotin, Neooncinotin, Isooncinotin und Pseudooncinotin in racemischer Form. 159. Mitteilung über Alkaloide
Armin Guggisberg,Peter Van Den Broek,Manfred Hesse,Hans Schmid,Fernand Schneider,Karl Bernauer +5 more
TL;DR: In this article, the authors synthesized four isomeric spermidine alkaloids: Oncinotine, Neooncinotine and Pseudoonincinotine in Racemic forms.