- The Reaction of Saccharin Derivatives with N,N-Diethylprop-1-ynamine: Formation of Cyclobutenyl Saccharinates and of a Spiro-oxete
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Saccharin and two equivalents of N,N-diethylprop-1-ynamine give a cyclobutenyl saccharinate (4) which, on bromination, gives the N-(cyclobutenyl cation)saccharin derivative (8), whose structure was established by X-ray crystallography ; N-methylsaccharin reacts with one equivalent of ynamine to yield the spiro-oxete (9): this represents the second isolation of such a stable oxete from reaction of an ynamine with a carbonyl group.
- Abramovitch, Rudolph A.,Ooi, Gino H. C.,Sun, Han-Li,Pierrot, Marcel,Baldy, Andre,Estienne, Jacques
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- Cross-coupling reactions of carbamoyl chlorides and Grignard reagents: A new rapid synthesis of tertiary amides
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Tributyl phosphine or nickel catalysts allow the cross-coupling reaction between N,N-dialkylcarbamoyl chlorides and alkyl or aryl Grignard reagents. This convenient and simple method affords tertiary amides with moderate to excellent yields in short reaction times. (C) 2000 Elsevier Science Ltd.
- Lemoucheux,Rouden,Lasne
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Read Online
- Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)
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This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
- Brittain, William D. G.,Cobb, Steven L.
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supporting information
p. 5793 - 5798
(2021/08/01)
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- Bromination of enamines from tertiary amides using the petasis reagent: A convenient one-pot regioselective route to bromomethyl ketones
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An original one-pot synthesis of bromomethyl ketones is achived using the Petasis reagent (dimethyltitanocene) as a key for enamine generation. Several amides were used to test the limits of the procedure by changing either the alkyl chain R or the amino portion of the starting materials. The enamines generated in situ were allowed to react with bromine at low temperature followed by hydrolysis to yield bromomethyl ketones in excellent yields (85 to 95%). Mechanistic details and optimum conditions for the reaction are briefly discussed. The present approach offers several advantages such as regioselectivity in enamine formation, good yields, mild reaction conditions, and ease of experimentation.
- Kobeissi, Marwan,Cherry, Khalil,Jomaa, Wissam
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supporting information
p. 2955 - 2965
(2013/09/02)
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- PROCESS FOR PREPARING SECONDARY AMIDES BY CARBONYLATION OF A CORRESPONDING TERTIARY AMINE
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The present invention relates to a process for preparing secondary amides with good selectivity by carbonylating a corresponding tertiary amine with carbon monoxide in a reaction mixture in the presence of a metal catalyst and in the presence of a halogen containing promoter. The metal catalyst comprises palladium. A same or even a much better catalytic activity can be obtained with palladium than with the much more expensive rhodium, especially when the palladium is used in a low concentration. Moreover, also a good selectivity can be achieved.
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Page/Page column 4
(2010/06/14)
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- Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures
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A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.
- Nery, Marcelo S.,Ribeiro, Renata P.,Lopes, Claudio C.,Lopes, Rosangela S. C.
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p. 272 - 276
(2007/10/03)
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- Cyclic and acyclic amidines and pharmaceutical compositions containing them for use as progesterone receptor binning agents
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Disclosed are cyclic and acyclic amidines, pharmaceutical compositions containing such amidines, and their use in treating or preventing progesterone receptor mediated diseases or conditions, such as osteopenia and osteoporosis.
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- Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides
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Reaction of 2-alkyl-4-enamides with I+ and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins with essentially no iodolactone by-product. The reaction appears to proceed through a cyclic imidate type intermediate. This methodology has been successfully employed for the synthesis of the epoxide intermediate of the orally active HIV-1 protease inhibitor MK-639 (indinavir sulfate).
- Maligres,Weissman,Upadhyay,Cianciosi,Reamer,Purick,Sager,Rossen,Eng,Askin,Volante,Reider
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p. 3327 - 3338
(2007/10/03)
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- Aminolysis of N-Acylpyrazoles
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1-Acylpyrazoles reacted with amines having a tiny substituted to afford the corresponding amides.The aminolysis with bulky amines was controlled to be retarded by the steric factors.Due to this steric interaction, the stereoselective aminolysis was observed.This selectivity of aminolysis should increase the utility of pyrazoles as auxiliary compounds in the synthetic loop.
- Kashima, Choji,Fukuchi, Iwao,Takahashi, Katsumi,Hosomi, Akira
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p. 1407 - 1412
(2007/10/02)
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- Ruthenium complex-catalyzed coupling of vinyl halides with olefins
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Ruthenium complexes such as Ru(COD)(COT) , catalyze the dehydrohalogenative coupling of vinyl halides with olefins to give the corresponding substituted dienes.Even the sp2-carbon-chloride bond of β-chlorostyrene is activated by ruthenium catalysts.
- Mitsudo, Take-aki,Takagi, Masakazu,Zhang, Shi-Wei,Watanabe, Yoshihisa
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p. 405 - 414
(2007/10/02)
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- Cobalt-catalyzed aminocarbonylation of geminal dihaloalkanes. Formation of 2-aminoamide and malonamide derivatives
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Co2(CO)8 catalyzed aminocarbonylation of geminal dihaloalkanes R2CX2 (R = H, CH3; X = Br, Cl) with NHEt2 affording R2C(NEt2)CONEt2 selectively in n-C6H14 using NEt3, while the yield of R2C(CONEt2)2 fairly increased in THF or benzene in aid of K2CO3.
- Miyashita,Kawashima,Kaji,Nomura,Nohira
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p. 781 - 784
(2007/10/02)
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- Process for one-step synthesis of amides
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A N-alkyl amide derivative is synthesized in one-step by reacting an olefin, nitrogen-containing compound and carbon monoxide with a catalyst comprising a rhodium-containing compound in the presence of water at a pressure of at least 500 psi and a temperature of at least 50° C.
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- The production of ethylene-derived chemicals from gaseous paraffins
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Ethylene-derived chemical products are produced from gaseous paraffinic hydrocarbons by the steps of: (I) feeding a gaseous paraffinic hydrocarbon, hydrogen and an oxygen-containing gas having a ratio of hydrocarbon to oxygen greater than the stoichiometric ratio for complete combustion to a partial oxidation zone maintained under conditions whereby partial oxidation and simultaneous cracking of the hydrocarbon occurs to form a product comprising acetylene, ethylene, carbon monoxide and hydrogen and recovering the product therefrom, (II) cooling the product from step (I) to a temperature below 500°C, (III) contacting under selective hydrogenation conditions the cooled product recovered from step (II) with a catalyst active in the presence of ethylene and carbon monoxide for the selective hydrogenation of acetylene to ethylene to form a product comprising ethylene, carbon monoxide and hydrogen, and (IV) either (i) separating the product from step (III) into ethylene, carbon monoxide and hydrogen, recovering the carbon monoxide and hydrogen and reacting the ethylene so-separated to form ethylene-derived products, or (ii) reacting ethylene, carbon monoxide, and hydrogen obtained in step (III) without separation to produce ethylene-derived products, or (iii) separating and recovering hydrogen from the product of step (III) and reacting the ethylene and carbon monoxide without further separation to produce ethylene-derived products.
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- N,O HETEROCYCLES. XXIII. THE REACTION OF SOME SUBSTITUTED HYDROXYLAMINES WITH THE ACTIVATED TRIPLE BOND
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The reaction of acylhydroxylamines with 1-(N,N-diethylamino)propyne gives rise to N-acyl-alaninediethylamides via 1,3-migration of the nitrogen moiety in the primary adduct likely having an N-O vinyl structure.
- Liguori, Angelo,Romeo, Giovanni,Sindona, Giovanni,Uccella, Nicola
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p. 617 - 620
(2007/10/02)
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- REACTION OF YNAMINES WITH BIFUNCTIONAL REAGENTS
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The reaction of 1-diethylamino- and 1-(ethylphenylamino)-1-propynes with aromatic and aliphatic bifunctional reagents was invectigated.In the reactions of the ynamines with aromatic binucleophiles and also with ethenolamine and ethylenediamine heterocyclic compounds of the benzodioxole, benzimidazoline, benzoxazole, benzothiazole, oxazoline, and imidazoline series are formed.The reactions of the ynamines with ethylene glycol and dithioglycol gave amino(alkoxy)alkenes and amino(alkylthio)-alkenes.
- Sokolova, E. A.,Maretina, I. A.,Petrov, A. A.
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p. 1500 - 1505
(2007/10/02)
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