The first synthesis of 2-tert-butyl-3-(1h-1,2,4-triazol-1-yl)-2hchromene-2-ol
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ZVEAGHINŢEVA, Marina; STÂNGACI, Eugenia; POGREBNOI, Serghei; GORINCIOI, Elena; BARBĂ, Alic; MACAEV, Fliur. The first synthesis of 2-tert-butyl-3-(1h-1,2,4-triazol-1-yl)-2hchromene-2-ol. In: Achievements and perspectives of modern chemistry. 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 249. ISBN 978-9975-62-428-2.
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Achievements and perspectives of modern chemistry 2019
Conferința "International Conference "Achievements and perspectives of modern chemistry""
Chişinău, Moldova, 9-11 octombrie 2019

The first synthesis of 2-tert-butyl-3-(1h-1,2,4-triazol-1-yl)-2hchromene-2-ol


Pag. 249-249

Zveaghinţeva Marina, Stângaci Eugenia, Pogrebnoi Serghei, Gorincioi Elena, Barbă Alic, Macaev Fliur
 
Institute of Chemistry
 
Disponibil în IBN: 12 noiembrie 2019


Rezumat

It is well known that the derivatives of 1,2,4-triazole posses fungicidal and regulating plant growth activity [1]. As the result of our studies, it was found that aldol condensation between N-vinyltriazolyl ketones and derivatives of salicylic aldehyde follows by two paths: 1) the final product of desired N-vinyltriazolyl ketone IS E- or Z-isomer, 2) the formation of unsaturated 1-benzopyran, also known as chromen [2] that forms through the subsequent cyclization of N-vinyl-triazolyl ketone. The reaction direction depends from the nature of substituent in initial triazolyl ketone and salicylic aldehyde. Recently, the synthesis of chromenes from initial bromylsulfonylbenzene and phenolic substrate using cesium carbonate as a catalyst was described [3]. Herein, we present the first example of the interaction between 1,2,4-triazolil ketone 1 [4] and salicylic aldehyde resulting a "hybrid" compound 2 with 1,2,4-triazole and 2H-chromene moieties. The reaction is conducted with catalytic amount of piperidine and acetic acid inboiling benzene followed by azeotropic water removal, resulted desired compound 2 (see scheme).formulaThe structure of compound 2 is confirmed by elemental analysis, IR-, NMR-spectroscopy and X-ray.