| 词条 | Lasri condensation |
| 释义 |
The Lasri condensation{{Primary source inline|date=November 2018}} is an organic chemistry reaction where chalcone reacts with a hydrazone to furnish an azine and 3,5-diphenyl-1H-pyrazole.[1] It is named after the Portuguese-Moroccan chemist Jamal Lasri.[2]{{Primary source inline|date=November 2018}} MechanismThe reaction is started with nucleophilic attack of the amino moiety of hydrazone 1 on the carbonyl group of (E)-1,3-diphenyl-2-propenone 3 to produce the azine intermediate 1-((E)-1,3-diphenylallylidene)-2-(diarylmethylene)hydrazine. This asymmetrical azine then undergoes nucleophilic attack from its diaryl imino sp2-carbon atom by the amino NH2 moiety of hydrazone 1 to afford a second intermediate where the C(sp3)—N bond is cleaved to furnish the symmetrical azine[3] 2. The other product, 1,3-diphenyl-2-propenone hydrazone 3a, cyclizes to afford 2,3-dihydro-3,5-diphenyl-1H-pyrazole[4] which is then rapidly dehydrogenated to yield 3,5-diphenyl-1H-pyrazole 4.[5] In this reaction hydrazone 1 is a source of nitrogen for 3,5-diphenyl-1H-pyrazole 4. Additionally, the reaction does not require the use of any catalyst or promoter. References1. ^{{cite journal|title = Metal-free and FeCl3-catalyzed synthesis of azines and 3,5-diphenyl-1H-pyrazole from hydrazones and/or ketones monitored by high resolution ESI+-MS|year = 2018|journal = Indian Journal of Chemistry - Section B|volume = 57|issue = 3|pages = 362-373|url = http://nopr.niscair.res.in/handle/123456789/43824|first = Jamal|last = Lasri|first2 = Ali I.|last2 = Ismail}} {{DEFAULTSORT:Lasri condensation}}2. ^{{cite web|url=http://www.kau.edu.sa/CVEn.aspx?Site_ID=0061741&Lng=EN|title=جمال العسري - CV|website=www.kau.edu.sa|accessdate=28 May 2017}} 3. ^{{cite journal|title = Experimental and theoretical study of crystal and molecular structure of 1,2-di(9H-fluoren-9-ylidene)hydrazine|year = 2016|journal = Journal of Molecular Structure|volume = 1121|pages = 35-45|doi = 10.1016/j.molstruc.2016.05.044|first1 = Jamal|last1 = Lasri|first2 = Naser E.|last2 = Eltayeb|first3 = Ali I.|last3 = Ismail|bibcode = 2016JMoSt1121...35L}} 4. ^{{cite journal|title = One-pot synthesis of 3,5-diphenyl-1H-pyrazoles from chalcones and hydrazine under mechanochemical ball milling|year = 2014|journal = Heterocycles|volume = 89|issue = 1|pages = 103-112|doi = 10.3987/COM-13-12867|first1 = Ze|last1 = Zhang|first2 = Ya-Jun|last2 = Tan|first3 = Chun-Shan|last3 = Wang|first4 = Hao-Hao|last4 = Wu}} 5. ^{{cite journal|title = New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating|year = 2008|journal = Journal of Heterocyclic Chemistry|volume = 45|issue = 2|pages = 503-505|doi = 10.1002/jhet.5570450231|first1 = Moha|last1 = Outirite|first2 = Mounim|last2 = Lebrini|first3 = Michel|last3 = Lagrenée|first4 = Fouad|last4 = Bentiss}} 6 : Name reactions|Condensation reactions|Pyrazoles|Azines|Functional groups|Simple aromatic rings |
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