TY  - JOUR
AU  - Petronijević, Jelena
AU  - Bugarčič, Zorica M.
AU  - Bogdanović, Goran A.
AU  - Stefanović, Srđan
AU  - Janković, Nenad
PY  - 2017
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1444
AB  - Innovative, efficient, clean, experimentally simple and environmentally friendly one-pot biocatalytic synthesis of two small libraries of 3,4-dihydro-2(1H)-quinoxalinones (4a-m) and 3,4-dihydro-1,4-benzoxazin-2-ones (5a, 5b, 5f and 5k-o) by heterocyclization of ethyl 2-hydroxy-4-alkyl(aryl)-4-oxo-2-butenoates (1a-o) or their corresponding salts (1a-o) with o-phenylenediamine (2) or o-aminophenol (3) in lemon juice as a solvent and a catalyst is presented. In all reactions where esters 1a-o are used for 24 h, very good-to-excellent yields were achieved, but the best yield was realized in the synthesis of 5a (97%) from 3 and 1a. The use of enolate salts (1a-o) instead of the corresponding esters 1a-o significantly reduced the reaction time (up to 6 h) and good-to-excellent yields were achieved. Groups with electron-donating or -withdrawing effects at the aromatic ring of the ester did not have significant influences on the yield of targeted products. In addition, several selected 3,4-dihydro-2(1H)-quinoxalinones and 3,4dihydro-1,4-benzoxazin-2-ones on a gram-scale in the yields up to 92% were synthesized. The presented synthetic strategy has produced smaller amount of waste without by-products and with excellent values of green chemistry metrics (atom efficiency, reaction mass efficiency, E-factor and EcoScale).
T2  - Green Chemistry
T1  - An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts
VL  - 19
IS  - 3
SP  - 707
EP  - 715
DO  - 10.1039/c6gc02893d
ER  - 

@article{
author = "Petronijević, Jelena and Bugarčič, Zorica M. and Bogdanović, Goran A. and Stefanović, Srđan and Janković, Nenad",
year = "2017",
abstract = "Innovative, efficient, clean, experimentally simple and environmentally friendly one-pot biocatalytic synthesis of two small libraries of 3,4-dihydro-2(1H)-quinoxalinones (4a-m) and 3,4-dihydro-1,4-benzoxazin-2-ones (5a, 5b, 5f and 5k-o) by heterocyclization of ethyl 2-hydroxy-4-alkyl(aryl)-4-oxo-2-butenoates (1a-o) or their corresponding salts (1a-o) with o-phenylenediamine (2) or o-aminophenol (3) in lemon juice as a solvent and a catalyst is presented. In all reactions where esters 1a-o are used for 24 h, very good-to-excellent yields were achieved, but the best yield was realized in the synthesis of 5a (97%) from 3 and 1a. The use of enolate salts (1a-o) instead of the corresponding esters 1a-o significantly reduced the reaction time (up to 6 h) and good-to-excellent yields were achieved. Groups with electron-donating or -withdrawing effects at the aromatic ring of the ester did not have significant influences on the yield of targeted products. In addition, several selected 3,4-dihydro-2(1H)-quinoxalinones and 3,4dihydro-1,4-benzoxazin-2-ones on a gram-scale in the yields up to 92% were synthesized. The presented synthetic strategy has produced smaller amount of waste without by-products and with excellent values of green chemistry metrics (atom efficiency, reaction mass efficiency, E-factor and EcoScale).",
journal = "Green Chemistry",
title = "An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts",
volume = "19",
number = "3",
pages = "707-715",
doi = "10.1039/c6gc02893d"
}

Petronijević, J., Bugarčič, Z. M., Bogdanović, G. A., Stefanović, S.,& Janković, N.. (2017). An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts. in Green Chemistry, 19(3), 707-715.
https://doi.org/10.1039/c6gc02893d

Petronijević J, Bugarčič ZM, Bogdanović GA, Stefanović S, Janković N. An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts. in Green Chemistry. 2017;19(3):707-715.
doi:10.1039/c6gc02893d .

Petronijević, Jelena, Bugarčič, Zorica M., Bogdanović, Goran A., Stefanović, Srđan, Janković, Nenad, "An enolate ion as a synthon in biocatalytic synthesis of 3,4-dihydro-2(1H)-quinoxalinones and 3,4-dihydro-1,4-benzoxazin-2-ones: lemon juice as an alternative to hazardous solvents and catalysts" in Green Chemistry, 19, no. 3 (2017):707-715,
https://doi.org/10.1039/c6gc02893d . .