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Synthesis of 3,4-dihydro-2H-1,3-benzoxazines by condensation of 2-hydroxyaldehydes and primary amines: Application to the synthesis of hydroxy-substituted and deuterium-labeled compounds

Publicated to:Synthetic Communications. 38 (14): 2316-2329 - 2008-01-01 38(14), doi: 10.1080/00397910802138629

Authors: Andreu R; Ronda JC

Affiliations

Rovira I Virgili University, Analytical Chemistry and Organic Chemistry Department, Faculty of Chemistry, Tarragona, Spain - Author
Rovira I Virgili University, Analytical Chemistry and Organic Chemistry Department, Faculty of Chemistry, Tarragona, Spain, Universitat Rovira I Virgili, Departament de Química Analítica I Química Orgànica, Campus de Sescelades, Carrer Marcellí Domingo s/ - Author

Abstract

Summary: We report the synthesis of several substituted 3,4-dihydro-2H-1,3- benzoxazines by simple ring closure of 2-hydroxybenzylamines with paraformaldehyde. The facile synthesis of the benzylamine precursors from commercially available salicylaldehyde derivatives affords a powerful general synthetic way to prepare a variety of substituted benzoxazines, avoiding the formation of undesirable oligomeric species, thus leading to a simple workup and improving the yield and purity of the final product. This straightforward method allows synthesis of hydroxy-substituted and deuterium-labeled 1,3-benzoxazines that are not attainable using other synthetic ways. Copyright © Taylor & Francis Group, LLC.

Keywords: 2 hydroxy n (4 hydroxyphenyl)benzylamine; 2 hydroxy n benzylbenzylamine; 2 hydroxy n methylbenzylamine; 2 hydroxy n phenylbenzylamine; 2,2 dideutero 3 phenyl 3,4 dihydro 2h 1,3 benzoxazine; 2,5 dihydroxy n phenylbenzylamine; 3 (4 hydroxyphenyl) 3,4 dihydro 2h 1,3 benzoxazine; 3 benzyl 3,4 dihydro 2h 1,3 benzoxazine; 3 methyl 3,4 dihydro 2h 1,3 benzoxazine; 3 pentadeuterophenyl 3,4 dihydro 2h 1,3 benzoxazine; 3 phenyl 3,4 dihydro 2h 1,3 benzoxazin 6 ol; 3 phenyl 3,4 dihydro 2h 1,3 benzoxazine; 4 [2h 1,3 benzoxazin 3(4h) il]phenol; 4,4 dideutero 3 phenyl 3,4 dihydro 2h 1,3 benzoxazine; 5,6,7,8 tetradeuterophenyl 3,4 dihydro 2h 1,3 benzoxazine; 6 hydroxy 3 phenyl 3,4 dihydro 2h 1,3 benzoxazine; Article; Benzoxazine derivative; Benzoxazine monomers; Benzylamine derivative; Chemical reaction; Deuterium; Deuterium labeling; Drug structure; Hydroxyaldehyde; Paraformaldehyde; Polymerization; Ring closing metathesis; Salicylaldehyde; Synthesis

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

Este trabajo ha sido citado 44 veces en WoS y 53 en Scopus.

Desde una perspectiva relativa, los impactos Normalizados conseguidos por la acumulación de citas arroja valores como: 53.00 (FWCI, Scopus), lo que indica que de manera comparada con trabajos en la misma disciplina y en el mismo año de publicación los ubica como trabajos citados por encima de la media.

Leadership analysis of institutional authors
Por otra parte, existe un liderazgo significativo ya que algunos de los autores pertenecientes a la institución aparecen como primer o último firmante, se puede apreciar en el detalle: Primer Autor (Andreu R) y Último Autor (Ronda Bargalló, Juan Carlos). Igualmente, el autor responsable de establecer las labores de correspondencia ha sido Ronda Bargalló, Juan Carlos.

Impact and social visibility