I<sub>2</sub>-Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides

Yu, Wenquan; Huang, Gang; Zhang, Yueteng; Liu, Hongxu; Dong, Lihong; Xiao, Yu; Li, Yujiang; Chang, Junbiao

doi:10.1021/jo401751h

Cited by 127 publications

(56 citation statements)

References 33 publications

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“…Study of the 1,3,4‐oxadiazole ring system is a mature subject,6–15 but calculation of the energetic properties of this series of compounds is relatively unexplored 16,17. Since the introduction of nitro groups into aromatic rings at the 2,5‐ positions of the 1,3,4‐oxadiazole ring raises the OB and is expected to raise the heats of formation of these compounds, we decided to synthesize a series of 2,5‐diaryl‐1,3,4‐oxadiazoles containing one, two or three nitro groups in each aromatic ring in order to study the effect of molecular composition on the energetic properties.…”

Section: Introductionmentioning

confidence: 99%

Two‐Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template‐Assisted Phase Transformation

Huang

Liu

et al. 2014

Angewandte Chemie

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Semiconducting nanosheets with microscale lateral size are attractive building blocks for the fabrication of electronic and optoelectronic devices. The phase‐controlled chemical synthesis of semiconducting nanosheets is of particular interest, because their intriguing properties are not only related to their size and shape, but also phase‐dependent. Herein, a facile method for the synthesis of phase‐pure, microsized, two‐dimensional (2D) CuSe nanosheets with an average thickness of approximately 5 nm is demonstrated. These hexagonal‐phased CuSe nanosheets were transformed into cubic‐phased Cu2−xSe nanosheets with the same morphology simply by treatment with heat in the presence of CuI cations. The phase transformation, proposed to be a template‐assisted process, can be extended to other systems, such as CuS and Cu1.97S nanoplates. Our study offers a new method for the phase‐controlled preparation of 2D nanomaterials, which are not readily accessible by conventional wet‐chemical methods.

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Section: Introductionmentioning

confidence: 99%

Two‐Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template‐Assisted Phase Transformation

Huang

Liu

et al. 2014

Angewandte Chemie

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“…for C 14 H 9 BrN 2 NaO (M+Na) + 322.9790, found 322.9785.2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole (3u).White solid (58 mg, 46%), mp: 120-121 o C; 1 H NMR (CDCl 3 , 400 MHz) δ 8.14-8.12 (m, 2H), 8.01 (d, J = 7.5 Hz, 1H), 7.53-7.47 (m, 4H), 7.11-7.06 (m, 2H), 3.99 (s, 3H) ppm; 13 C NMR (CDCl 3 ,100 MHz) δ 164.3, 163.3, 157.9, 133.0, 131.5, 130.4, 129.0, 126.9, 124.1, 120.7, 111.9, 56.0 ppm; HRMS (ESI): Calcd. for C 15 H 12 N 2 NaO 2 (M+Na) + 275.0791, found 275.0794.2-(naphthalen-1-yl)-5-phenyl-1,3,4-oxadiazole (3v) 14. Yellow solid (110 mg, 81%), mp: 120-122 o C; 1 H NMR (CDCl 3 , 400 MHz) δ 9.30 (d, J = 8.4 Hz, 1H), 8.27 (d, J = 7.3 Hz, 1H), 8.20-8.17 (m, 2H), 8.04 (d, J = 8.2 Hz, 1H), 7.94 (d, J = 8.1 Hz, 1H), 7.73-7.69 (m, 1H), 7.62-7.52 (m, 5H) ppm; 13 C NMR (CDCl 3 ,100 MHz) δ 164.…”

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confidence: 99%

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

et al. 2015

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A metal- and base-free protocol for one-pot synthesis of 2,5-diaryl 1,3,4-oxadiazoles via a radical-promoted cross-dehydrogenative coupling strategy was developed. This reaction involved the N-acylation of aryl tetrazoles with aryl aldehydes, followed by thermal rearrangement. A wide range of aryl tetrazoles and aryl aldehydes survived the reaction conditions to deliver the corresponding products in moderate to good yields.

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“…Na terceira aula experimental foi dada continuidade à rota sintética para obtenção do heterociclo 1,3,4-oxadiazol (4), sendo o mesmo obtido através da ciclização oxidativa da acil-hidrazona (3), preparada na aula prática anterior, empregando-se iodo molecular como agente oxidante. 27 Para esta síntese a fonte de calor convencional foi alterada, sendo também utilizada a irradiação de micro-ondas e, como na etapa anterior, o heterociclo foi obtido com um tempo de reação consideravelmente curto (10 minutos) e com alto rendimento (84%). A determinação do ponto de fusão permitiu evidenciar que o protótipo 1,3,4-oxadiazol (4) foi sintetizado, uma vez que apresentou faixa de fusão (154-157 °C) semelhante à descrita na literatura para esta molécula (152-155 °C).…”

Section: Resultsunclassified

Abordagem Didática Para O Desenvolvimento De Moléculas Bioativas: Regra Dos Cinco De Lipinski E Preparação De Heterociclo 1,3,4-Oxadiazol Em Forno De Micro-Ondas Doméstico

Santos¹,

Gonsalves²,

Araújo³

2017

Quim. Nova

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. In Brazil, the development of new chemical entities (NEQ) is still limited to small advances in the academic and public research sectors, the authors understand that this is a sector of the pharmaceutical industry that needs encouragement. Accepting that education transforms society, educate students in the development of bioactive molecules, it's a way to stimulate the national pharmaceutical industry to invest in the sector. Thus, this work brings a didactic sequence, applicable in undergraduate courses, which exemplifies some stages of development of the NEQ through its rational planning. The synthesis of a 1,3,4-oxadiazole heterocycle was planned and its potentiality assessed through the Lipinski's Rule of Five (RO5), using the ChemSpider ® database. Once in accordance with RO5, the heterocycle was prepared using a simple and accessible methodology, using microwaves for domestic use as heating source. The 2-phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazole was synthesized by oxidative cyclization of acylhydrazone and an overall yield of 90%. So was possible to demonstrate in a practical way some steps for the development of a substance with potential biological activity and thus to attract greater interest of undergraduate students by this follow-up of the Medicinal Chemistry. INTRODUÇÃODo ponto de vista econômico, as inovações podem se tornar o diferencial para a competitividade de empresas e países. Dentro deste cenário, a indústria farmacêutica é uma das mais lucrativas em razão da busca constante por produtos inovadores. Existem quatro estágios tecnológicos na indústria farmacêutica, sendo estes: Estágio I -Pesquisa e Desenvolvimento (P&D); Estágio II -Produção de Farmoquímicos; Estágio III -Produção de Especialidades Farmacêuticas; e Estágio IV -Marketing e Comercialização das Especialidades Farmacêuticas. A descoberta de novas moléculas com potencial terapêutico (novas entidades quí-micas -NEQ) faz parte do Estágio Tecnológico I, uma atividade que compreende a pesquisa básica de screening, o desenho molecular e os estudos farmacológicos. 1No Brasil, tanto as indústrias nacionais quanto as subsidiárias de multinacionais atuam apenas nos Estágios Tecnológicos III e IV, ou seja, há formulação de medicamentos e comercialização, contudo, praticamente quase a totalidade das matérias-primas deve ser importada. Embora o país possua uma indústria de medicamentos bastante desenvolvida, sua capacidade tecnológica para gerar inovações ainda não é satisfatória, ficando as atividades de P&D basicamente restritas a setores acadêmicos e públicos de pesquisa. 1 A Química Medicinal é uma área de estudo que visa o desenvolvimento de novos fármacos, e assim, fornece meios para a obtenção de NEQ. A síntese orgânica colabora com este processo promovendo a obtenção das moléculas propostas. A formação de recursos humanos capacitados para o desenvolvimento de NEQ é uma maneira de colaborar com o setor nacional de P&D de fármacos, área considerada estratégica do ponto de vista social, econômico e político. Considerando que, de 70 a 8...

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I₂-Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides

Cited by 127 publications

References 33 publications

Two‐Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template‐Assisted Phase Transformation

Two‐Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template‐Assisted Phase Transformation

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

Abordagem Didática Para O Desenvolvimento De Moléculas Bioativas: Regra Dos Cinco De Lipinski E Preparação De Heterociclo 1,3,4-Oxadiazol Em Forno De Micro-Ondas Doméstico

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I2-Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides

Cited by 127 publications

References 33 publications

Two‐Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template‐Assisted Phase Transformation

Two‐Dimensional CuSe Nanosheets with Microscale Lateral Size: Synthesis and Template‐Assisted Phase Transformation

One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di-tert-butyl Peroxide Promoted N-Acylation of Aryl Tetrazoles with Aldehydes

Abordagem Didática Para O Desenvolvimento De Moléculas Bioativas: Regra Dos Cinco De Lipinski E Preparação De Heterociclo 1,3,4-Oxadiazol Em Forno De Micro-Ondas Doméstico

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I₂-Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides