Next Article in Journal
Oxidative Folding in the Mitochondrial Intermembrane Space in Human Health and Disease
Previous Article in Journal
Optimization of β-Glucosidase, β-Xylosidase and Xylanase Production by Colletotrichum graminicola under Solid-State Fermentation and Application in Raw Sugarcane Trash Saccharification
Article Menu

Export Article

Open AccessArticle
Int. J. Mol. Sci. 2013, 14(2), 2903-2915; doi:10.3390/ijms14022903

Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters

1
Department of Chemistry, Faculty of Superior Studies Cuautitlan, Field 1, Autonomous National University of Mexico, Cuautitlan Izcalli, State of Mexico, 54740, Mexico
2
Institute of Chemistry, Autonomous National University of Mexico, University City, Coyoacan, D.F., 04510, Mexico
*
Author to whom correspondence should be addressed.
Received: 7 November 2012 / Revised: 19 December 2012 / Accepted: 4 January 2013 / Published: 30 January 2013
(This article belongs to the Section Green Chemistry)
View Full-Text   |   Download PDF [221 KB, uploaded 19 June 2014]   |  

Abstract

Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho, meta and para), were obtained using a green approach, involving H-4CR and B-3CR practices, in the presence of ethanol, which is a green solvent, and using three comparatively different modes of activation (mantle heating, yield 3%–7% in 24 h, Infrared Radiation (IR) irradiation, yield 12%–17% in 12 h, and microwave irradiation, yield 18%–80%, requiring very low reaction times of 0.25–0.33 h). In addition, as a green-approach is offered, a convenient analysis, of the 12 green chemistry principles for the overall procedure was performed. Finally, since all the products are new, characterizations were carried out using common analytic procedures (1H, 11B, and 13C NMR, FAB+MS, HRMS, and IR). The accurate mass data of unexpected ions related to interactions between thioglycerol and the expected products, in the FAB+-mode, enabled unequivocal characterization of the target molecules.
Keywords: multicomponent reaction; green chemistry; twelve principles; boron-containing-Hantzsch and Biginelli esters; microwave and infrared irradiation; matrix-ion interaction; FAB+MS multicomponent reaction; green chemistry; twelve principles; boron-containing-Hantzsch and Biginelli esters; microwave and infrared irradiation; matrix-ion interaction; FAB+MS
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Martínez, J.; Romero-Vega, S.; Abeja-Cruz, R.; Álvarez-Toledano, C.; Miranda, R. Green Approach—Multicomponent Production of Boron—Containing Hantzsch and Biginelli Esters. Int. J. Mol. Sci. 2013, 14, 2903-2915.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top