Synthesis and identification of thiazolidinones from 3- picolylamine and thiazinanones from 1-(2-aminoethyl)piperidine

Submitted by Mírian Farias Ribeiro (mirianfribeiro@yahoo.com.br) on 2022-05-12T13:02:39Z No. of bitstreams: 2 license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5) Duval.pdf: 3023684 bytes, checksum: 13812d0d07cb26d4e6108881f83a3637 (MD5) Approved for entry into archive by Aline Batista (alinehb.ufpel@gmail.com) on 2022-05-16T11:28:54Z (GMT) No. of bitstreams: 2 Duval.pdf: 3023684 bytes, checksum: 13812d0d07cb26d4e6108881f83a3637 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5) Made available in DSpace on 2022-05-16T11:28:54Z (GMT). No. of bitstreams: 2 Duval.pdf: 3023684 bytes, checksum: 13812d0d07cb26d4e6108881f83a3637 (MD5) license_rdf: 0 bytes, checksum: d41d8cd98f00b204e9800998ecf8427e (MD5) Previous issue date: 2015-04-13 Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES O presente trabalho apresenta a síntese de 1,3-tiazolidin-4-onas: a) via metodologia de aquecimento térmico convencional através de reação multicomponente entre 3-(aminometil)piridina (3-picolilamina), quinze benzaldeídos (R-PhCHO, onde R= 2-NO2, 3-NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4- Cl, 2-OCH3, 3-OCH3, 4-OCH3, 4-CH3, 2-OH, 3-OH e 4-OH) e ácido mercaptoacético por quatro horas, em refluxo de tolueno, com rendimentos de 59 a 97%; b) via ultrassom através da reação multicomponente “one-pot” entre 3-(aminometil)piridina (3-picolilamina), seis benzaldeídos (R-PhCHO, onde R= 4-NO2, 4-F, 4-Cl, 4-OCH3, 4-CH3 e 4-OH) e o ácido mercaptoacético por dez minutos em tolueno com rendimentos de 30 a 78%. O trabalho também apresenta a síntese de 1,3-tiazinan-4-onas: a) via metodologia de aquecimento térmico convencional através de reação multicomponente “one-pot” entre 2-(aminoetil)piperidina, dezenove benzaldeídos (R-PhCHO, onde R= 3-NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2- OCH3, 3-OCH3, 4-OCH3, 4-CH3, 3-Cl, 2,4-Cl, 2,6-Cl, 2,3-OCH3, 2,4-OCH3, 2,5- OCH3, 3,4-OCH3 e 2-Cl,6-F) e ácido mercaptopropiônico por seis horas em refluxo de tolueno com rendimentos de 38 a 99%; b) via ultrassom através da reação multicomponente entre 2-(aminoetil)piperidina, dezenove benzaldeídos (R-PhCHO, onde R= 3-NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2-OCH3, 3-OCH3, 4-OCH3, 4-CH3, 3-Cl, 2,4-Cl, 2,6-Cl, 2,3-OCH3, 2,4-OCH3, 2,5-OCH3, 3,4-OCH3 e 2-Cl,6-F) e ácido mercaptopropiônico por trinta minutos em tolueno com rendimentos de 37 a 86%. Os compostos sintetizados tiveram seus pontos de fusão determinados e foram caracterizados e identificados por Espectrometria de Massas e Espectroscopia de Ressonância Magnética Nuclear de 1H e 13C. This work presents the synthesis of 1,3-thiazolidin-4-ones: a) by conventional thermal heating through multicomponent reaction between 3- (aminomethyl)pyridine (3-picolylamine), fifteen arenealdehydes (R-PhCHO, where R= 2-NO2, 3-NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2-OCH3, 3-OCH3, 4- OCH3, 4-CH3, 2-OH, 3-OH e 4-OH) and mercaptoacetic acid for four hours in refluxing toluene with yields 59 to 97%; b) by ultrasound through multicomponent one-pot reaction between 3-(aminomethyl)pyridine (3- picolylamine), six arenealdehydes (R-PhCHO, where R= 4-NO2, 4-F, 4-Cl, 4- OCH3, 4-CH3 e 4-OH) and mercaptoacetic acid for ten minutes in toluene with yields 30 to 78%. This work also presents the synthesis of 1,3-thiazinan-4-ones: a) by conventional thermal heating through multicomponent one-pot reaction between 2-(aminoethyl)piperidine, nineteen arenealdehydes (R-PhCHO, where R= 3- NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2-OCH3, 3-OCH3, 4-OCH3, 4-CH3, 3-Cl, 2,4-Cl, 2,6-Cl, 2,3-OCH3, 2,4-OCH3, 2,5-OCH3, 3,4-OCH3 and 2-Cl,6-F) and mercaptopropionic acid for six hours in refluxing toluene with yields 38 to 99%; b) by ultrasound through multicomponent reaction between 2- (aminoethyl)piperidine, nineteen arenealdehydes (R-PhCHO, where R= 3-NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2-OCH3, 3-OCH3, 4-OCH3, 4-CH3, 3-Cl, 2,4-Cl, 2,6-Cl, 2,3-OCH3, 2,4-OCH3, 2,5-OCH3, 3,4-OCH3 and 2-Cl,6-F) and mercaptopropionic acid for thirty minutes in toluene with yields 37 to 86%. The synthesized compounds had evaluated their melting points and were charactetized and identified by mass spectrometry and nuclear magnetic resonance spectroscopy of 1H and 13C.