4927-53-1Relevant academic research and scientific papers
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
supporting information, p. 15593 - 15598 (2021/10/12)
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis
Henry, Martyn C.,Sutherland, Andrew
supporting information, p. 2766 - 2770 (2020/03/30)
One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.
Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles
Gupton, John T.,Shimozono, Alex,Crawford, Evan,Ortolani, Joe,Clark, Evan,Mahoney, Matt,Heese, Campbell,Noble, Jeffrey,Mandry, Carlos Perez,Kanters, Rene,Dominey, Raymond N.,Goldman, Emma W.,Sikorski, James A.,Fisher, Daniel C.
, p. 2650 - 2663 (2018/04/23)
Highly functionalized pyrroles with appropriate regiochemical functionality represent an important class of marine natural products and potential drug candidates. We describe herein a detailed study of the reaction of α-aminoacid esters with vinylogous amides and also β-halovinylaldehydes for the regiospecific synthesis of 2,3,4-trisubstituted and 1,2,3,4-tetrasubstituted pyrroles. Since the vinylogous amides and β-halovinylaldehydes are readily available precursors, rapid access to a wide variety of unsymmetrically substituted pyrroles is accomplished via this methodology.
3-Phenyl-isochromens, bridged stilbenes
Unterhalt,Fahrig
, p. 679 - 686 (2007/10/03)
Tamoxifen and other stilbene derivatives bind to the estrogen receptor 3-Phenyl-isochromens are bridged stilbenes and might do the same. The related compounds 12-18 are synthesised by reducing 2-benzopyrylium perchlorates 6-11; they have only weak activit
Influence of Alkoxyalkyl Substituents in the Regioselective Lithiation of the Benzene Ring
Napolitano, Elio,Giannone, Enrico,Fiaschi, Rita,Marsili, Antonio
, p. 3653 - 3657 (2007/10/02)
The concomitant presence of an alkoxyalkyl group (α-alkoxyalkyl, α- or β-dialkoxyalkyl) and of an alkoxy group in the relative positions 1 and 3 in a benzene ring generally permits an easy lithiation of position 2 by proton-metal exchange with n-butyllithium; the only aromatic compound tested, bearing a β-alkoxyalkyl group, gave, however, extensive decomposition in the metalation step.Reaction of the metalated species with an electrophile (such as carbon dioxide or ethyl chloroformate) leads to the corresponding substituted products in good to excellent yields.The following transformations are described: 3,4-dimethoxybenzyl α-ethoxyethyl ether (1) into 6,7-dimethoxyphthalide (15); 3,4-(methylenedioxy)benzyl α-ethoxyethyl ether (2) into 6,7-(methylenedioxy)phthalide (16); 3,4-dimethoxybenzyl methyl ether (3) into ethyl 2-(methoxymethyl)-5,6-dimethoxybenzoate (18) and into ethyl 2-(chloromethyl)-5,6-dimethoxybenzoate (20); 3,4-(methylenedioxy)benzyl methyl ether (4) into ethyl 2-(methoxymethyl)-5,6-(methylenedioxy)benzoate (19) and into ethyl 2-(chloromethyl)-5,6-(methylenedioxy)benzoate (21); 3,4-dimethoxybenzaldehyde dimethyl acetal (5) into 5,6-dimethoxyphthalaldehydic acid (22); 3,4-(methylenedioxy)benzaldehyde dimethyl acetal (6) into 5,6-(methylenedioxy)phthalaldehydic acid (23); (3,4-dimethoxyphenyl)acetaldehyde dimethyl acetal (7) into ethyl 2-(2,2-dimethoxyethyl)-5,6-dimethoxybenzoate (25); 3,4,4'-trimethoxydeoxybenzoin ethylene acetal (10) into 2-(ethoxycarbonyl)-3,4,4'-trimethoxydeoxybenzoin (26); 4,3',4'-trimethoxydeoxybenzoin ethylene acetal (11) into 2'-(ethoxycarbonyl)-4,3',4'-trimethoxydeoxybenzoin (27); 3,4,3',4'-tetramethoxydeoxybenzoin ethylene acetal (12) into a mixture of 3-(3,4-dimethoxybenzylidene)-6,7-dimethoxyphthalide (28) and 3-(3,4-dimethoxyphenyl)-7,8-dimethoxyisocoumarin (29).The dioxole ring of methylenedioxy-substituted benzenes is sometimes unstable under these metalation conditions, and partial decomposition usually causes the yields to be lower than those in the case of the corresponding methoxy-substituted benzenes.Many of the products listed above, which have been already prepared by other methods, are more conveniently obtained by the present approach.
