dc.creator | Janković, Nenad Ž. | |
dc.creator | Stefanović, Srđan M. | |
dc.creator | Petronijević, Jelena | |
dc.creator | Joksimović, Nenad | |
dc.creator | Novaković, Slađana B. | |
dc.creator | Bogdanović, Goran A. | |
dc.creator | Muškinja, Jovana | |
dc.creator | Vraneš, Milan | |
dc.creator | Ratković, Zoran R. | |
dc.creator | Bugarčić, Zorica M. | |
dc.date.accessioned | 2018-10-23T11:11:37Z | |
dc.date.available | 2018-10-23T11:11:37Z | |
dc.date.issued | 2018 | |
dc.identifier.issn | 2168-0485 | |
dc.identifier.uri | http://pubs.acs.org/doi/10.1021/acssuschemeng.8b03127 | |
dc.identifier.uri | https://vinar.vin.bg.ac.rs/handle/123456789/7886 | |
dc.description.abstract | The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum's acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2-C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels-Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold. © Copyright 2018 American Chemical Society. | en |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172011/RS// | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172034/RS// | |
dc.rights | restrictedAccess | |
dc.source | ACS Sustainable Chemistry and Engineering | |
dc.subject | Biginelli-Atwal reaction | en |
dc.subject | solvent-free | en |
dc.subject | dihydrouracil | en |
dc.subject | diazoles | en |
dc.subject | tautomer-selective | en |
dc.subject | short C=N bond | en |
dc.subject | green metrics | en |
dc.title | Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry | en |
dc.type | article | en |
dc.rights.license | ARR | |
dcterms.abstract | Јанковић, Ненад; Богдановић, Горан A; Стефановић, Срђан; Петронијевић, Јелена; Јоксимовић, Ненад; Новаковић, Слађана Б; Мушкиња, Јована; Вранеш, Милан; Ратковић, Зоран; Бугарчић, Зорица; | |
dc.rights.holder | © Copyright 2018 American Chemical Society | |
dc.citation.volume | 6 | |
dc.citation.issue | 10 | |
dc.citation.spage | 13358 | |
dc.citation.epage | 13366 | |
dc.identifier.wos | 000446413100084 | |
dc.identifier.doi | 10.1021/acssuschemeng.8b03127 | |
dc.citation.rank | aM21 | |
dc.description.other | Supporting data: [http://vinar.vin.bg.ac.rs/handle/123456789/7888] | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-85053342893 | |