Synthesis of 5,6-dihydropyridin-2(1H)-ones, 1,5,6,8,8a- hexahydroisoquinolin-3(2H)-ones and 4a,5,6,7,8,8a-hexahydroquinolin-2(1H)-ones by intramolecular Wittig reaction

Molecules

Volumn 7, Issue 2, 2002, Pages 124-128

  Fisyuk, Alexander S ^a   Poendaev, Nikolai V ^a  

^a OMSK STATE UNIVERSITY   (Russian Federation)

Author keywords

5,6 Dihydropyridin 2(1H) one; Intramolecular cyclization; N (3 oxoalkyl)chloroacetamide; Wittig reaction

Indexed keywords

ACETAMIDE DERIVATIVE; PYRIDONE DERIVATIVE; QUINOLINE DERIVATIVE; SODIUM CHLORIDE; TRIPHENYLPHOSPHINE;

ARTICLE; CYCLIZATION; MOLECULE; STEREOSPECIFICITY; SYNTHESIS; WITTIG REACTION;

EID: 2442587574     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/70200124     Document Type: Article

References (12)

1. Fisyuk, A. S.; Bundel, Yu. G. 5,6-Dihydropyridin-2(1H)-ones and 5,6-dihydropyridine-2(1H)-thiones. Chem. Heterocycl. Compd. (N. Y.), 1999, 35, 125-145.
2. Davis, D.A.; Gribble, G.W. A regioselective Diels-Alder synthesis of ellipticine. Tetrahedron Lett., 1990, 31, 1081-1084.
3. Amat, M.; Llor, N.; Bosch, J.; Solans, X. Preparation of Enantiopure 6-(3-Indolyl)-2-piperidones and Conjugate Additions to a 3,4-Didegidro Derivative. Tetrahedron, 1997, 53, 719-730.
4. Heron, B.M. Heterocycles from Intramolecular Wittig, Horner and Wadsworth-Emmons Reactions. Heterocycles, 1995, 41, 2357-2385.
5. Marson, Ch.M.; Fallah, A. Catalytic C-amidoalkylations: synthesis of β-amido aldehydes by three-component condensations. Chem. Commun., 1998, 83-84.
6. Lora-Tamayo, M.; Madroñero, R.; Leipprand, H. Beitrag zum chemischen Verhalten der 4H-1,3-Oxazine. Chem. Ber., 1964, 97, 2244-2250.
7. Ikeda, K.; Terao, Y.; Sekiya, M. New Syntheses of α-N- Alkylacetamidomethylated Carbonyl Compounds. Chem. Pharm. Bull., 1981, 29, 1156-1159.
8. Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Synthesis of diastereo- and enantiomerically pure α-amino-g-oxo acid esters by reaction of acyliminoacetates with enamines derived from 6-membered ketones. Tetrahedron, 1985, 41, 1693-1701.
9. Fisyuk, A.S.; Vorontsova, M.A.; Sagitullin, R.S. A New Synthesis of 3-Phenyl-5,6-Dihydropyridin-2(1H)-ones. Mendeleev Commun., 1993, 249-251.
10. Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Kutsuna, T.; Saigo, K. Triphenylphosphine/Germanium (IV) Chloride Combination: A New Agent for the Reduction of α-Bromo Carboxylic Acid Derivatives. Tetrahedron Lett., 1998, 39, 1203-1206.
11. Fisyuk, A. S.; Poendaev, N. V.; Bundel, Y.G. A New Route for Synthesis of 5,6-Dihydropyridine-2(1H)-ones, Pyridones-2 and (4-Hydroxy-2-oxopiperidyl-3) pyridinium chlorides by Intramolecular Cyclization of N-3- Oxoalkylchloroacetamides Derivatives. Mendeleev Commun., 1998, 12-14.
12. Zaugg, H. E. α-Amidoalkylation at Carbon: Recent Advances - Part II. Synthesis, 1984, 181-211.