Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones
Sinteza i ispitivanje efekta rastvarača na UV spektre 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona
Апстракт
A number of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones from cyanoacetamide and the corresponding alkyl ethyl acetoacetates were synthesized according to modified literature procedures. The alkyl ethyl acetoacetates were obtained by the reaction of C-alkylation of ethyl acetoacetate. An investigation of the reaction conditions for the synthesis of 4-methyl-3-cyano-6-hydroxy-2-pyridone from cyanoacetamide and ethyl acetoacetate in eight different solvents was also performed. The ultraviolet absorption spectra of synthesized pyridones were measured in nine different solvents in the range 200-400 nm. The effects of solvent polarity and hydrogen bonding on the absorption spectra are interpreted by means of linear solvation energy relationships using a general equation of the form ν = νo + sπ*+aα+ bβ, where π* is a measure of the solvent polarity, α is the scale of the solvent hydrogen bond donor acidities and β is the scale of the solvent hydrogen bond acceptor basicities. .
U okviru rada je izvršena sinteza 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i alkiletilacetacetata u prisustvu kalijum-hidroksida u metanolu kao rastvaraču. Alkiletilacetacetati su dobijeni reakcijom C-alkilovanja etilacetacetata odgovarajućim alkilhaloghenidima. Takođe je izvršeno ispitivanje reakcionih uslova za sintezu 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i etilacetacetata u prisustvu KOH, NaOH i K2CO3 u različitim rastvaračima. IR, 1H-NMR i UV podaci su dati za sintetizovane piridone, a IR i 1H-NMR podaci su dati za sintetizovane alkiletilacetacetate. Apsorpcioni spektri 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona su određeni u devet rastvarača različitih polarnosti u opsegu 200-400 nm. Uticaj polarnosti rastvarača kao i efekat vodonične veze proučavani su metodom linearne korelacije solvatacionih efekata odnosno jednačinom oblika ν = νo + sπ* + aα + bβ, u kojoj je ν apsorpciona frekvenca, π* mera efekata solvatacije... vezana za polarnost rastvarača, α mera uspostavljanja vodonične veze sa proton-donorskim rastvaračima, a β mera vodonične veze ostvarene sa proton-akceptorskim rastvaračima. .
Кључне речи:
alkylation / ethyl acetoacetate / alkyl ethyl acetoacetates synthesis / 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones / spectroscopy / cyclization / ultraviolet absorption spectra / solvent effects / linear solvation energy relationshipsИзвор:
Journal of the Serbian Chemical Society, 2001, 66, 8, 507-516Издавач:
- Serbian Chemical Society, Belgrade
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Mijin, Dušan AU - Ušćumlić, Gordana AU - Valentić, Nataša PY - 2001 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/390 AB - A number of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones from cyanoacetamide and the corresponding alkyl ethyl acetoacetates were synthesized according to modified literature procedures. The alkyl ethyl acetoacetates were obtained by the reaction of C-alkylation of ethyl acetoacetate. An investigation of the reaction conditions for the synthesis of 4-methyl-3-cyano-6-hydroxy-2-pyridone from cyanoacetamide and ethyl acetoacetate in eight different solvents was also performed. The ultraviolet absorption spectra of synthesized pyridones were measured in nine different solvents in the range 200-400 nm. The effects of solvent polarity and hydrogen bonding on the absorption spectra are interpreted by means of linear solvation energy relationships using a general equation of the form ν = νo + sπ*+aα+ bβ, where π* is a measure of the solvent polarity, α is the scale of the solvent hydrogen bond donor acidities and β is the scale of the solvent hydrogen bond acceptor basicities. . AB - U okviru rada je izvršena sinteza 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i alkiletilacetacetata u prisustvu kalijum-hidroksida u metanolu kao rastvaraču. Alkiletilacetacetati su dobijeni reakcijom C-alkilovanja etilacetacetata odgovarajućim alkilhaloghenidima. Takođe je izvršeno ispitivanje reakcionih uslova za sintezu 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i etilacetacetata u prisustvu KOH, NaOH i K2CO3 u različitim rastvaračima. IR, 1H-NMR i UV podaci su dati za sintetizovane piridone, a IR i 1H-NMR podaci su dati za sintetizovane alkiletilacetacetate. Apsorpcioni spektri 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona su određeni u devet rastvarača različitih polarnosti u opsegu 200-400 nm. Uticaj polarnosti rastvarača kao i efekat vodonične veze proučavani su metodom linearne korelacije solvatacionih efekata odnosno jednačinom oblika ν = νo + sπ* + aα + bβ, u kojoj je ν apsorpciona frekvenca, π* mera efekata solvatacije vezana za polarnost rastvarača, α mera uspostavljanja vodonične veze sa proton-donorskim rastvaračima, a β mera vodonične veze ostvarene sa proton-akceptorskim rastvaračima. . PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones T1 - Sinteza i ispitivanje efekta rastvarača na UV spektre 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona EP - 516 IS - 8 SP - 507 VL - 66 UR - https://hdl.handle.net/21.15107/rcub_technorep_390 ER -
@article{ author = "Mijin, Dušan and Ušćumlić, Gordana and Valentić, Nataša", year = "2001", abstract = "A number of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones from cyanoacetamide and the corresponding alkyl ethyl acetoacetates were synthesized according to modified literature procedures. The alkyl ethyl acetoacetates were obtained by the reaction of C-alkylation of ethyl acetoacetate. An investigation of the reaction conditions for the synthesis of 4-methyl-3-cyano-6-hydroxy-2-pyridone from cyanoacetamide and ethyl acetoacetate in eight different solvents was also performed. The ultraviolet absorption spectra of synthesized pyridones were measured in nine different solvents in the range 200-400 nm. The effects of solvent polarity and hydrogen bonding on the absorption spectra are interpreted by means of linear solvation energy relationships using a general equation of the form ν = νo + sπ*+aα+ bβ, where π* is a measure of the solvent polarity, α is the scale of the solvent hydrogen bond donor acidities and β is the scale of the solvent hydrogen bond acceptor basicities. ., U okviru rada je izvršena sinteza 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i alkiletilacetacetata u prisustvu kalijum-hidroksida u metanolu kao rastvaraču. Alkiletilacetacetati su dobijeni reakcijom C-alkilovanja etilacetacetata odgovarajućim alkilhaloghenidima. Takođe je izvršeno ispitivanje reakcionih uslova za sintezu 4-metil-3-cijano-6-hidroksi-2-piridona iz cijanoacetamida i etilacetacetata u prisustvu KOH, NaOH i K2CO3 u različitim rastvaračima. IR, 1H-NMR i UV podaci su dati za sintetizovane piridone, a IR i 1H-NMR podaci su dati za sintetizovane alkiletilacetacetate. Apsorpcioni spektri 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona su određeni u devet rastvarača različitih polarnosti u opsegu 200-400 nm. Uticaj polarnosti rastvarača kao i efekat vodonične veze proučavani su metodom linearne korelacije solvatacionih efekata odnosno jednačinom oblika ν = νo + sπ* + aα + bβ, u kojoj je ν apsorpciona frekvenca, π* mera efekata solvatacije vezana za polarnost rastvarača, α mera uspostavljanja vodonične veze sa proton-donorskim rastvaračima, a β mera vodonične veze ostvarene sa proton-akceptorskim rastvaračima. .", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones, Sinteza i ispitivanje efekta rastvarača na UV spektre 5-supstituisanih 4-metil-3-cijano-6-hidroksi-2-piridona", pages = "516-507", number = "8", volume = "66", url = "https://hdl.handle.net/21.15107/rcub_technorep_390" }
Mijin, D., Ušćumlić, G.,& Valentić, N.. (2001). Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 66(8), 507-516. https://hdl.handle.net/21.15107/rcub_technorep_390
Mijin D, Ušćumlić G, Valentić N. Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones. in Journal of the Serbian Chemical Society. 2001;66(8):507-516. https://hdl.handle.net/21.15107/rcub_technorep_390 .
Mijin, Dušan, Ušćumlić, Gordana, Valentić, Nataša, "Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6-hydroxy-2-pyridones" in Journal of the Serbian Chemical Society, 66, no. 8 (2001):507-516, https://hdl.handle.net/21.15107/rcub_technorep_390 .