Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation

Abstract The clean synthesis of 6-cyano-2,2-dimethyl-2- H -1-benzopyran epoxide starting from 3-methyl-2-butenal is reported using recyclable catalysts. H₄PMo₁₁VO₄₀ (PMo₁₁V) and (PyH)₃HPMo₁₁VO₄₀ (Py₃ –PMo₁₁V) Keggin-type heteropolyacids were used to synthesize 6-cyano-2,2-dimethyl-2- H -1-benzopyran...

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Autores principales: Romanelli, Gustavo Pablo, Sathicq, Ángel Gabriel, Vázquez, Patricia Graciela, Villa, Aída Luz, Alarcón, Edwin, Grajales, Edwing, Cubillos, Jairo
Formato: Articulo
Lenguaje:Inglés
Publicado: 2015
Materias:
Ciencias Exactas
Química
Heteropolyacids
Jacobsen-type catalyst
Sustainable synthesis
6-Cyano-2,2-dimethyl-2-H-1-benzopyran
Chromene epoxide
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/128792
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-128792
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Ciencias Exactas
Química
Heteropolyacids
Jacobsen-type catalyst
Sustainable synthesis
6-Cyano-2,2-dimethyl-2-H-1-benzopyran
Chromene epoxide
spellingShingle Ciencias Exactas
Química
Heteropolyacids
Jacobsen-type catalyst
Sustainable synthesis
6-Cyano-2,2-dimethyl-2-H-1-benzopyran
Chromene epoxide
Romanelli, Gustavo Pablo
Sathicq, Ángel Gabriel
Vázquez, Patricia Graciela
Villa, Aída Luz
Alarcón, Edwin
Grajales, Edwing
Cubillos, Jairo
Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation
topic_facet Ciencias Exactas
Química
Heteropolyacids
Jacobsen-type catalyst
Sustainable synthesis
6-Cyano-2,2-dimethyl-2-H-1-benzopyran
Chromene epoxide
description Abstract The clean synthesis of 6-cyano-2,2-dimethyl-2- H -1-benzopyran epoxide starting from 3-methyl-2-butenal is reported using recyclable catalysts. H₄PMo₁₁VO₄₀ (PMo₁₁V) and (PyH)₃HPMo₁₁VO₄₀ (Py₃ –PMo₁₁V) Keggin-type heteropolyacids were used to synthesize 6-cyano-2,2-dimethyl-2- H -1-benzopyran in two steps with 35% yield. This is an alternative procedure to the traditional methodology with pyridine or picoline as catalyst, where 6-cyano-2,2-dimethyl-2- H -1-benzopyran is obtained by condensation of 4-cyanophenol with 1,1-diethoxy-3-methyl-2-butene. The 6-cyano-2,2-dimethyl-2- H -1-benzopyran epoxide was obtained using Jacobsen-type catalysts, and in situ generated dimethyldioxirane (DMD) as oxidizing agent, that in comparison to m -CPBA/4-NMO and NaOCl/4-PPNO did not degrade the catalyst. In presence of 4-phenylpyridine N -oxide (4-PPNO) at 4 °C, enantioselectivities of 87% for 3S,4S-epoxide and 68% for 3R,4R-epoxide were obtained with the S,S- and R,R-Jacobsen catalysts, respectively. Overall yield was approximately 17% for 3S,4S-epoxide.
format Articulo
Articulo
author Romanelli, Gustavo Pablo
Sathicq, Ángel Gabriel
Vázquez, Patricia Graciela
Villa, Aída Luz
Alarcón, Edwin
Grajales, Edwing
Cubillos, Jairo
author_facet Romanelli, Gustavo Pablo
Sathicq, Ángel Gabriel
Vázquez, Patricia Graciela
Villa, Aída Luz
Alarcón, Edwin
Grajales, Edwing
Cubillos, Jairo
author_sort Romanelli, Gustavo Pablo
title Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation
title_short Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation
title_full Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation
title_fullStr Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation
title_full_unstemmed Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and its subsequent enantioselective epoxidation
title_sort green synthesis of 6-cyano-2,2-dimethyl-2-h-1-benzopyran and its subsequent enantioselective epoxidation
publishDate 2015
url http://sedici.unlp.edu.ar/handle/10915/128792
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