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An efficient and inexpensive device for undergraduate chemistry classes aiming teaching the photolytic synthesis concepts

Quim. Nova 2014, 37(1), 164-167,  2014

Um reator fotoquímico barato e eficiente para experimentos de química

Ramon Kenned Sousa AlmeidaI; Cláudia MartelliI; Gilson Herbert Magalhães DiasI; Julio Cesar Araujo da SilvaII, *

An efficient and inexpensive device for undergraduate chemistry classes aiming teaching the photolytic synthesis concepts. This device presents simplicity, low costs, class-compatible reaction times and good yields.

Ramon Kenned Sousa Almeidaa , Cláudia Martellia , Gilson Herbert Magalhães Diasa e Julio Cesar Araujo da Silvab,* a Instituto de Química, Universidade Estadual de Campinas, 13083-970 Campinas – SP, Brasil b Instituto Federal de Ciência e Tecnologia de Santa Catarina, Estrada do Senadinho, s/no , Centro, 88625-000 Urupema – SC, Brasil

A CHEAP AND EFFICIENT PHOTOCHEMICAL REACTOR FOR CHEMICAL EXPERIMENTS. In this work, we present an efficient and inexpensive device for undergraduate chemistry classes aimed at teaching and learning the photolytic synthesis concepts. A photochemical reactor was tested for the synthesis of the organometallic compound enneacarbonyldiiron from iron pentacarbonyl in acetic acid, and its formation evidenced by FTIR analysis. Although similar devices have been described in other studies, none of these offered the simplicity, low cost, class-compatible reaction times and good yields afforded by the procedure reported herein.

Keywords: photochemistry; reactor; enneacarbonyldiiron.

 

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Instituto de Química, Universidade Estadual de Campinas

 

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Instituto Federal de Ciência e Tecnologia de Santa Catarina, Estrada do Senadinho

Campus Palhoça-Bilingue. Atualizado por Rafael Batista. O Instituto Federal de Educação, Ciência e Tecnologia de Santa Catarina …

 

 

Aberto o concurso do Instituto Federal de Educação, Ciência e Tecnologia de Santa Catarina (IFSC). A seleção visa prover um total de 145 vagas.

 

Instituto Federal de Educação, Ciência e Tecnologia – Campus Rio do Sul – Cantagalo

Synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides: evaluation of antioxidant and antimicrobial activities

Quim. Nova 2014, 37(8), 1297-1301

Synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides: evaluation of antioxidant and antimicrobial activities

Juan I. Sarmiento-SánchezI,*; Julio Montes-AvilaII; Adrián Ochoa-TeránIII; Francisco Delgado-VargasII; Victor Wilson-CorralI; Sylvia P. Díaz-CamachoII; Fernando García-PáezI; Pedro Bastidas-BastidasIV
IFaculty of Engineering, Autonomous University of Sinaloa, Blvd. of the Americas S/N, 80040, Campus Culiacán, Culiacán, Sinaloa, México IIFaculty of Chemical-Biological Sciences, Autonomous University of Sinaloa, Blvd. of the Americas S/N, 80040, Campus Culiacán, Culiacán, Sinaloa, México IIICentro de Graduados e Investigación en Química, Instituto Tecnológico de Tijuana, Blvd. Alberto Limón Padilla S/N, 22500, Tijuana, B.C., México IVLaboratorio de Análisis de Residuos de Plaguicidas, Centro de Investigación en Alimentación y Desarrollo, A.C., Unidad Culiacán, México

In this work we reported the synthesis of benzoxazine-2,4-diones derivatives and their evaluation of antioxidant and antimicrobial activities.

http://dx.doi.org/10.5935/0100-4042.20140201

http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422014000800006&lng=en&nrm=iso

A facile one-step synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides and TMSA was described. This paper determines their antimicrobial activity against nine human bacterial pathogens by the broth microdilution method; antioxidant activity by DPPH• inactivation and a ferric-reducing power assay; and toxicity by a brine shrimp, Artemia salina, assay. The 1H-benzoxazine-2,4-dione yields were in the range of 57 to 98%. The novel compound 1H-pyrazino[2,3-][1,3]oxazine-2,4-dione 4cshowed the highest antioxidant capacity (DPPH 35.4% and FRAP 0.063 µmol TEs/µmol).

Keywords: 1H-benzoxazine-2,4-dione; antimicrobial activity; antioxidant activity; toxicity.

1H-3,1-benzoxazine-2,4-quinone   1H-[3,1]benzoxazine-2,4-dione 2H-3,1-benzoxazine-2,4(1H)-dione 1H-3,1-benzoxazine-2,4-dione 1H-3,1-benzoxazin-2,4-dion 1H-3,1-ベンゾキサジン-2,4-ジオン

SMILES   O=C1NC2=C(C=CC=C2)C(=O)O1

Synthesis Reference(s) for 1H-3,1-benzoxazine-2,4-quinone
Organic Syntheses, Coll. Vol. 3, p. 488, 1955

The Journal of Organic Chemistry, 48, p. 2, 1983

1H-3,1-benzoxazine-2,4-quinone (4a). (For full characterization see lit.);28,29 CAS number: 118-48-9; yield 85%; white solid; Rf0.58 (petroleum ether/EtOAc 1:1 v/v);

1H-NMR (200 MHz, DMSO-d6): δ 11.74 (br s, 1H), 7.91 (dd, J1=8.07, J2=1.1 Hz, 1H), 7.74 (td, J1=7.79, J2=1.28 Hz, 1H), 7.25 (m, 2H);

13C-NMR (50 MHz, DMSO-d6): δ 159.9, 147.1, 141.4, 136.9, 128.9, 123.5, 115.3;

CG-MS m/z: 164 [M+H]+

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Centro de Investigación en Alimentación y Desarrollo

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El Centro de Investigación en Alimentación y Desarrollo A.C. (CIAD), ofrecerá un curso

University of Sinaloa

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Instituto Tecnológico de Tijuana

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Enzymatic resolution of antidepressant drug precursors in an undergraduate laboratory

EducaçãoQuim. Nova 2015, 38(2), 285-287

Enzymatic resolution of antidepressant drug precursors in an undergraduate laboratory

Luís M. R. SolanoI; Nuno M. T. LourençoII,*

This paper describes a multi-step chemo-enzymatic synthesis of antidepressant drug precursors.

http://dx.doi.org/10.5935/0100-4042.20140306

Publicado online: novembro 13, 2014
Quim. Nova, Vol. 38, No. 2, 285-287, 2015
*e-mail: nmtl@tecnico.ulisboa.pt
ENZYMATIC RESOLUTION OF ANTIDEPRESSANT DRUG PRECURSORS IN AN UNDERGRADUATE LABORATORY
Luís M. R. Solanoa and Nuno M. T. Lourençob,* a Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal b Departamento de Bioengenharia, Instituto de Biotecnologia e Bioengenharia, Instituto Superior Técnico, Av. Rovisco Pais, 1, 1049-001 Lisboa, Portugal
Recebido em 07/07/2014; aceito em 17/09/2014; publicado na web em 13/11/2014
The use of biocatalysts in synthetic chemistry is a conventional methodology for preparing enantiomerically enriched compounds. Despite this fact, the number of experiments in chemical teaching laboratories that demonstrate the potential of enzymes in synthetic organic chemistry is limited. We describe a laboratory experiment in which students synthesized a chiral secondary alcohol that can be used in the preparation of antidepressant drugs. This experiment was conducted by individual students as part of a Drug Synthesis course held at the Pharmacy Faculty, Lisbon University. This laboratory experiment requires six laboratory periods, each lasting four hours. During the first four laboratory periods, students synthesized and characterized a racemic ester using nuclear magnetic resonance spectroscopy and gas chromatography. During the last two laboratory periods, they performed enzymatic hydrolysis resolution of the racemic ester using Candida antarctica lipase B to yield enantiomerically enriched secondary alcohol. Students successfully prepared the racemic ester with a 70%-81% overall yield in three steps. The enzymatic hydrolysis afforded (R)- secondary alcohol with good enantioselectivity (90%–95%) and reasonable yields (10%–19%). In these experiments, students were exposed to theoretical and practical concepts of aromatic acylation, ketone reduction, esterification, and enzymatic hydrolysis. Keywords: sec-alcohols; esters; lípase; enantiomers; resolution.
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A rant about data quality: machines first, humans second…

Originally posted on Cheminformatics 2.0:

GraphicalAbstractRecently one of my papers emerged through the publication system of Journal of Cheminformatics, entitled “Machines first, humans second: on the importance of algorithmic interpretation of open chemistry data“, co-authored with Antony Williams and Sean Ekins, and incorporated into the JC Bradley Memorial Issue. Spoiler alert: the paper is about how if you’re publishing open lab notebook data without adhering to rigorously defined standards for machine readability, then you’re mostly wasting your time, and arguably making the open data situation even worse than it already is. The tone of the article is a bit less polite than I normally try to be, so fair warning, but it’s all for a good cause.

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