Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)-Î³-Pelargonolactone
- (R)-4-Menthen-3-one anti-Oxime and Its Transformation under Beckman Rearrangement Conditions. Kharisov, R. Ya.; Latypova, E. R.; Talipov, R. F.; Muslukhov, R. R.; Ishmuratov, G. Yu.; Tolstikov, G. A. // Chemistry of Natural Compounds;Nov/Dec2003, Vol. 39 Issue 6, p569
(R)-4-Menthenone anti-oxime was synthesized for the first time. Its transformations under Beckman rearrangement conditions were studied.
- Symmetrical and Unsymmetrical Bis-1,1'-(3,4-dihydroisoquinolines). Glushkov, V. A.; Karmanov, V. I.; Shklyaev, Yu. V. // Chemistry of Heterocyclic Compounds;Apr2005, Vol. 41 Issue 4, p475
3,3,-Dialkyl-1-cyano-3,4-dihydroisoquinolines were prepared by Beckmann defragmentation of ethyl a-(3,3-dialkyl-3,4-dihydroisoquinol-1-yl)-a-hydroximinoacetates and they take part in a Ritter reaction to form substituted bis-1,1'-(3,4-dihydroisoquinolines).
- Plant Coumarins. 2. Beckmann Rearrangement of Oreoselone E- and Z-Oximes. Bagryanskaya, I.; Gatilov, Yu.; Osadchii, S.; Martynov, A.; Shakirov, M.; Shul'ts, E.; Tolstikov, G. // Chemistry of Natural Compounds;Nov2005, Vol. 41 Issue 6, p657
Oximation of oreoselone to produce a mixture the E- and Z-oximes was investigated. The crystal and molecular structures of oreoselone Z-oxime and the Beckmann rearrangement product of oreoselone E- or Z-oximes and PCl5, 7-(1-chloro-2-methylpropoxy)-2-oxo-2H-1-benzopyran-6-carbonitrile, were...
- Anomalous Beckmann Reaction of 4-Aryl-2,7,7-trimethyl-5-oxo-5,6,7,8-tetrahydroquinoline Oximes in Polyphosphoric Acid. 1. New Synthesis of 1-Ethoxycarbonyl-2,5,5-trimethyl-5,6-dihydro-4H-pyrido[2,3,4-k,l]acridines. Tolkkunov, S. V.; Khyzhan, A.I.; Dulenko, V. I. // Chemistry of Heterocyclic Compounds;Dec2003, Vol. 39 Issue 12, p1627
Transformations of oximes of 4-aryl-2,7,7-trimethyl-5-oxo-5,6,7,8-tetrahydroquinolines in PPA have been studied. It is shown that the reaction, depending on substituent at position 4 of quinoline ring, can occur in three directions: aromatization of the saturated ring (Semmler-Wolff...
- Beckmann Rearrangement of Dimethylcyclopentanonepimarate Oxime. Tret'yakova, E. V.; Flekhter, O. B.; Galin, F. Z.; Baikova, I. P.; Tolstikov, G. A. // Chemistry of Natural Compounds;Jan/Feb2003, Vol. 39 Issue 1, p16
Beckmann rearrangement of dimethylcyclopentanonepimarate-15-oxime 2 was used to produce lactam 3 or seco-nitrile 4, depending on the conditions. The structures of the synthesized compounds were confirmed by IR and NMR spectroscopies.
- Synthesis of N-containing drimane sesquiterpenoids from 11-dihomodriman-8Î±-ol-12-one. Kuchkova, K. I.; Aryku, A. N.; Vlad, P. F.; Deleanu, K.; Nikolescu, A. // Chemistry of Natural Compounds;Sep2010, Vol. 46 Issue 4, p539
Beckmann reaction products of 11-dihomodriman-8Î±-ol-12-one oxime with AcO in pyridine, 86% HPO, p-TsCl in pyridine, and PCl in ether were investigated. It has been found that the major product from treatment of the oxime with AcO is the oxime acetate. Reaction of the oxime with 86% HPO gave...
- New Benzo- and Thieno-fused Spirolactams. Stanetty, Peter; Sigl, Beatrix; Schnürch, Michael; Mihovilovic, Marko D. // Acta Chimica Slovenica;2009, Vol. 56 Issue 3, p513
A short and efficient approach leading to new spiro compounds joining benzo- and thieno-fused lactams and piperidine is presented. Various derivatives were prepared by alkylation of 1-methylpiperidinecarboxylates, cyclization to spiroketones, and subsequent Beckmann rearrangement of the...
- Silica-Supported Dichlorophosphate Catalyzed Beckmann Rearrangement and Dehydration of Oximes Under Microwave Irradiation. Zheng Li; Zhong Lu // Letters in Organic Chemistry;Sep2008, Vol. 5 Issue 6, p495
Silica-supported dichlorophosphate had been proved to be an efficient, recoverable and reusable catalyst for Beckmann rearrangement of a variety of ketoximes and dehydration of various aldoximes in THF under microwave irradiation. This protocol has advantages of high conversion, high...
- Accessibility and Interaction of Surface OH Groups in Microporous and Mesoporous Catalysts Applied for Vapor-Phase Beckmann Rearrangement of Oximes. Marthala, V. R. Reddy; Frey, J.; Hunger, M. // Catalysis Letters;Mar2010, Vol. 135 Issue 1/2, p91
1H and 2H MAS NMR spectroscopy were utilized for investigating the interaction of surface complexes upon adsorption of cyclohexanone and cyclododecanone oxime on MFI-type zeolites and [Al]SBA-15. Signals of hydrogen-bonded and protonated complexes were identified and evidenced the diffusion of...