SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS

The Suzuki-Miyaura cross-coupling reaction has successfully been applied for the synthesis of 4,4'- [6-(diethylamino)-1,3,5-triazine-2,4-diyl]diphenol (4a), 4,4'-(pyrimidine-4,6-diyl)diphenol (4b), 4,4'-(pyridine-2,6-diyl)diphenol (4c). The reaction of 4,6-dichloro-N,N-diethyl-1,3,5-t...

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Autores principales:	NASEER,MUHAMMAD MOAZZAM, ABBAS,ASGHAR, HAMEED,SHAHID, FARM,MUHAMMAD
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2014
Materias:	dichloroheteroaryls Suzuki-Miyaura cross-coupling demethylation dinucleophiles
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000400018
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spelling	oai:scielo:S0717-970720140004000182015-01-09SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTSNASEER,MUHAMMAD MOAZZAMABBAS,ASGHARHAMEED,SHAHIDFARM,MUHAMMAD dichloroheteroaryls Suzuki-Miyaura cross-coupling demethylation dinucleophiles The Suzuki-Miyaura cross-coupling reaction has successfully been applied for the synthesis of 4,4'- [6-(diethylamino)-1,3,5-triazine-2,4-diyl]diphenol (4a), 4,4'-(pyrimidine-4,6-diyl)diphenol (4b), 4,4'-(pyridine-2,6-diyl)diphenol (4c). The reaction of 4,6-dichloro-N,N-diethyl-1,3,5-triazin-2-amine (1a), 4,6-dichloropyrimidine (1b) and 2,6-dichloropyridine (1c) with p-methoxyphenylboronic acid (2) in the presence of palladium catalyst followed by demethylation reaction furnished the desired products in good to excellent yields. To test the reactivity of these nucleophiles, the compound 4a was further reacted with cyanuric chloride to get trimeric fragment (5a). All the compounds were characterized by their physical, spectral (¹H and 13C NMR and Mass) and microanalytical data. These dinucleophilic fragments (4a-4c) having triazine, pyrimidine and pyridine rings, respectively, are excellent future candidates for the construction of large functional hetero-atom bridged macrocycles for diverse applications in host-guest chemistry, supramolecular catalysis, self-assembly and other related fields of supramolecular chemistry in addition to their potential in medicinal chemistry.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.59 n.4 20142014-12-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000400018en10.4067/S0717-97072014000400018
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	dichloroheteroaryls Suzuki-Miyaura cross-coupling demethylation dinucleophiles
spellingShingle	dichloroheteroaryls Suzuki-Miyaura cross-coupling demethylation dinucleophiles NASEER,MUHAMMAD MOAZZAM ABBAS,ASGHAR HAMEED,SHAHID FARM,MUHAMMAD SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS
description	The Suzuki-Miyaura cross-coupling reaction has successfully been applied for the synthesis of 4,4'- [6-(diethylamino)-1,3,5-triazine-2,4-diyl]diphenol (4a), 4,4'-(pyrimidine-4,6-diyl)diphenol (4b), 4,4'-(pyridine-2,6-diyl)diphenol (4c). The reaction of 4,6-dichloro-N,N-diethyl-1,3,5-triazin-2-amine (1a), 4,6-dichloropyrimidine (1b) and 2,6-dichloropyridine (1c) with p-methoxyphenylboronic acid (2) in the presence of palladium catalyst followed by demethylation reaction furnished the desired products in good to excellent yields. To test the reactivity of these nucleophiles, the compound 4a was further reacted with cyanuric chloride to get trimeric fragment (5a). All the compounds were characterized by their physical, spectral (¹H and 13C NMR and Mass) and microanalytical data. These dinucleophilic fragments (4a-4c) having triazine, pyrimidine and pyridine rings, respectively, are excellent future candidates for the construction of large functional hetero-atom bridged macrocycles for diverse applications in host-guest chemistry, supramolecular catalysis, self-assembly and other related fields of supramolecular chemistry in addition to their potential in medicinal chemistry.
author	NASEER,MUHAMMAD MOAZZAM ABBAS,ASGHAR HAMEED,SHAHID FARM,MUHAMMAD
author_facet	NASEER,MUHAMMAD MOAZZAM ABBAS,ASGHAR HAMEED,SHAHID FARM,MUHAMMAD
author_sort	NASEER,MUHAMMAD MOAZZAM
title	SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS
title_short	SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS
title_full	SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS
title_fullStr	SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS
title_full_unstemmed	SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS
title_sort	suzuki-miyaura cross-coupling reaction of dichloro-heteroaromatics: synthesis of functionalized dinucleophilic fragments
publisher	Sociedad Chilena de Química
publishDate	2014
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072014000400018
work_keys_str_mv	AT naseermuhammadmoazzam suzukimiyauracrosscouplingreactionofdichloroheteroaromaticssynthesisoffunctionalizeddinucleophilicfragments AT abbasasghar suzukimiyauracrosscouplingreactionofdichloroheteroaromaticssynthesisoffunctionalizeddinucleophilicfragments AT hameedshahid suzukimiyauracrosscouplingreactionofdichloroheteroaromaticssynthesisoffunctionalizeddinucleophilicfragments AT farmmuhammad suzukimiyauracrosscouplingreactionofdichloroheteroaromaticssynthesisoffunctionalizeddinucleophilicfragments
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SUZUKI-MIYAURA CROSS-COUPLING REACTION OF DICHLORO-HETEROAROMATICS: SYNTHESIS OF FUNCTIONALIZED DINUCLEOPHILIC FRAGMENTS

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