129118-10-1Relevant articles and documents
L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones
Kumar, Dinesh,Kommi, Damodara N.,Chopra, Pradeep,Ansari, Md Imam,Chakraborti, Asit K.
, p. 6407 - 6413,7 (2020/09/16)
A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.
Dimethylformamide dimethyl acetal in heterocyclic synthesis: Synthesis of polyfunctionally substituted pyridine derivatives as precursors to bicycles and polycycles [1,2]
Abu-Shanab, Fathi A.,Hessen,Mousa
, p. 787 - 791 (2008/03/29)
(Chemical Equation Presented) Polysubstituted pyridines 11a,c and 12 were prepared by the reaction of benzoylacetone with dimethylformamide dimethyl acetal followed by treatment with cyanothioacetamide 9a, cyanoacetamide 9b and the anion of malononitrile dimmer 9c in dry DMF. When the reaction was carried out in ethanol as a solvent and piperidine as a base afforded 14a,b. Thienopyridines 16a,b were prepared by the reaction of pyridinethiones 11a and 14a with 2-chloro-N-p-tolyl-acetamide (15). Further reaction of thienopyridines 16a,b with either DMFDMA or nitrous acid to gave 17a,b and 18a,b respectively. The reaction of pyridine derivative 11c with hydrazine and phenylhydrazine afforded the tricyclic compounds 19a,b.
6-Substituted pyranone compounds and their use as pharmaceuticals
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, (2008/06/13)
Compounds are described of the formula STR1 in which R1 is COOR5, CONHR5, cyano, 5-tetrazolyl or R6, where R5 is hydrogen or C1-8 alkyl and R6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C1-6 alkyl, C1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C1-4 alkylsulphinyl, C1-4 alkylsulphonyl, N(R5)2, NHCOR5 and SR5 ; R2 is R6 or --CH=CH--R6 when R1 is COOR5, CONHR5, cyano or 5-tetrazolyl, or R2 is --CH=CH--R6 when R1 is R6 ; R3 is hydrogen, C1-6 alkyl, halogen, hydroxy or --OCH2 R6 ; and R4 is hydrogen, C1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.
THE SYNTHESIS AND REARRANGEMENT OF EPOXYPYRONES
Ross, William J.,Todd, Alec,Clark, Barry P.,Morgan, Sarah E.,Baldwin, Jack E.
, p. 2207 - 2208 (2007/10/02)
The oxidation of 5-acyl-4-oxo-pyran-2-carboxylic acid esters 1,2 to novel epoxypyrones and subsequent rearrangement to the previously inaccesible 6-substituted-5-hydroxy or 5-chloropyrones 6 - 9 are described.
