Show simple item record

dc.creatorJanković, Nenad Ž.
dc.creatorStefanović, Srđan M.
dc.creatorPetronijević, Jelena
dc.creatorJoksimović, Nenad
dc.creatorNovaković, Slađana B.
dc.creatorBogdanović, Goran A.
dc.creatorMuškinja, Jovana
dc.creatorVraneš, Milan
dc.creatorRatković, Zoran
dc.creatorBugarčić, Zorica M.
dc.date.accessioned2018-10-23T11:11:37Z
dc.date.available2018-10-23T11:11:37Z
dc.date.issued2018
dc.identifier.issn2168-0485 (print)
dc.identifier.urihttp://pubs.acs.org/doi/10.1021/acssuschemeng.8b03127
dc.identifier.urihttp://vinar.vin.bg.ac.rs/handle/123456789/7886
dc.description.abstractThe 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.
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172011/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172034/RS//
dc.rightsrestrictedAccess
dc.sourceACS Sustainable Chemistry & Engineering
dc.subjectBiginelli-Atwal reactionen
dc.subjectsolvent-freeen
dc.subjectdihydrouracilen
dc.subjectdiazolesen
dc.subjecttautomer-selectiveen
dc.subjectshort C=N bonden
dc.subjectgreen metricsen
dc.titleWater-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistryen
dc.typearticleen
dc.rights.licenseARR
dcterms.abstractЈанковић, 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.volume6
dc.citation.issue10
dc.citation.spage13358
dc.citation.epage13366
dc.identifier.wos000446413100084
dc.identifier.doi10.1021/acssuschemeng.8b03127
dc.description.otherSupporting data: [http://vinar.vin.bg.ac.rs/handle/123456789/7888]
dc.type.versionpublishedVersion
dc.identifier.scopus2-s2.0-85053342893


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record