- Ruthenium-catalyzed intramolecular hydrocarbamoylation of allylic formamides: Convenient access to chiral pyrrolidones
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An attractive strategy for the synthesis of saturated nitrogen-containing heterocycles is described herein, involving the implementation of ruthenium-catalyzed intramolecular hydrocarbamoylation of olefins. The process proceeds by formal C-H bond cleavage
- Armanino, Nicolas,Carreira, Erick M.
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p. 6814 - 6817
(2013/06/05)
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- APPLICATIONS OF THE THERMAL ENE REACTION OF ALDEHYDE t-BUTYL- AND PHENYL- HYDRAZONES
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The Thermal Ene reaction of aldehyde t-butyl- and phenyl- hydrazones with enophiles gave C-trapped azo-adducts which can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, γ-alkyl-2-pyrrolidones, and γ-amino-esters.
- Baldwin, Jack E.,Adlington, Robert M.,Jain, Ashok U.,Kolhe, Jayant N.,Perry, Matthew W. D.
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p. 4247 - 4252
(2007/10/02)
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- Michael Additions of Hydrazones for Carbon-Carbon Bond Formation
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The lithium salts of t-butyl- and trityl-hydrazones react with methyl crotonate to form C-trapped azo-esters and similar products were observed from a thermal ene-reaction of aldehyde t-butylhydrazones with methyl acrylate or acrylonitrile, and aldehyde phenylhydrazones with methyl acrylate; these products can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, saturated esters, γ-alkyl-2-pyrrrolidones, and γ-amino-esters.
- Baldwin, Jack E.,Adlington, Robert M.,Bottaro, Jeffrey C.,Jain, Ashok U.,Kolhe, Jayant N.,et al.
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p. 1095 - 1096
(2007/10/02)
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- CATALYTIC REDUCTION OF 3-(4,4-DIMETHYL-5-KETO-3-ISOXAZOLE)PROPIONIC ACID AND ITS DERIVATES
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Catalytic hydrogenation of 3-(4,4-dimethyl-5-keto-3-isoxazole)propionic acid (1) in glacial acetic acid in the presence of 5percent palladium on charcoal gives 4-amino-5-methylhexanoic acid (2).Reductions of the corresponding esters, methyl 3-(4,4-dimethyl-5-keto-3-isoxazole)propionate (3) and amide, 3-(4,4-dimethyl-5-keto-3-isoxazole)propionamide (4) afford, however, γ-isopropylbutyrolactam (5).Reductions of 1 and 3 in aqueous acetic acid give 4-keto-5-methylhexanoic acid (6) and methyl 4-keto-5-methylhexanoate (7), respectively.On the other hand amide 4 is converted to2-hydroxy-5-isopropylidene-Δ1-pyrroline (8).Compound 8 is also obtained if 4 is reduced in acetic acid containing a small amount of hydrogen chloride.
- Feuer, Henry,Scholl, Philip C.
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- A NOVEL REACTION OF α,γ-DINITRO COMPOUNDS. TRANSFORMATION OF METHYL 4,6-DINITRO-5,5-DIMETHYLHEXANOATE TO 2,2-DIMETHYL-3-OXIMINOADIPATE AND SUBSEQUENT CYCLIZATION TO 3-(4,4-DIMETHYL-5-KETO-3-ISOXAZOLE)PROPIONIC ACID
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Methyl 4,6-dinitro-5,5-dimethylhexanoate (2) is converted by catalytic quantities of sodium methoxide and ammonia to dimethyl 2,2-dimethyl-3-oximinoadipate (10) and 2,2-dimethyl-3-oximinoadipamide (11), respectively.On treatment with dilute acid, compounds 10 and 11 are readily cyclized to 3-(4,4-dimethyl-5-keto-3-isoxazole)propionic acid (3).Compound 3 is also obtained directly from compound 2 on treatment with base and subsequent acidification.
- Feuer, Henry,Halasa, Adel F.
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p. 1281 - 1288
(2007/10/02)
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