Microwave Assisted Reactions of Fluorescent Pyrrolodiazine Building Blocks.
Costel Moldoveanu, Dorina Amariucai-Mantu, Violeta Mangalagiu, Vasilichia Antoci, Dan Maftei, Ionel I Mangalagiu, Gheorghita Zbancioc
Author Information
Costel Moldoveanu: Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd, 700506 Iasi, Romania. costel.moldoveanu@uaic.ro. ORCID
Dorina Amariucai-Mantu: Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd, 700506 Iasi, Romania. dorina.mantu@uaic.ro.
Violeta Mangalagiu: Institute of Interdisciplinary Research CERNESIM Centre, Alexandru Ioan Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania. violeta.mangalagiu@uaic.ro. ORCID
Vasilichia Antoci: Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd, 700506 Iasi, Romania. vasilichia.antoci@uaic.ro.
Dan Maftei: Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd, 700506 Iasi, Romania. dan.maftei@chem.uaic.ro. ORCID
Ionel I Mangalagiu: Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd, 700506 Iasi, Romania. ionelm@uaic.ro. ORCID
Gheorghita Zbancioc: Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd, 700506 Iasi, Romania. gheorghita.zbancioc@uaic.ro. ORCID
We report here the synthesis and optical spectral properties of several new pyrrolodiazine derivatives. The luminescent heterocycles were synthesized by 1,3-dipolar cycloaddition reactions between N-alkylated pyridazine and methylpropiolate or dimethyl acetylenedicarboxylate (DMAD). The pyrrolopyridazine derivatives are blue emitters with moderate quantum yields (around 25%) in the case of pyrrolopyridazines and negligible yet measurable emission for pyrrolophthalazines. In a subsequent step towards including the pyrrolodiazine moiety, given its spectral properties in various macromolecular frameworks such as biological molecules, a subset of the synthetized compounds has been subjected to α-bromination. A selective and efficient way for α-bromination in heterogeneous catalysis of pyrrolodiazine derivatives under microwave (MW) irradiation is presented. We report substantially higher yields under MW irradiation, whereas the solvent amounts required are at least five-fold less compared to classical heating.
