2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible to further synthetically useful conversions is the condensation of commercially available methyl 2,3-dibromopropionate with already suitably functionalized catechol. Here, we obtain methyl 8- and 5-nitro-1,4-benzodioxane-2-carboxylate by reaction of methyl 2,3-dibromopropionate with 3-nitrocatechol. After separation, the two positional isomers could be unequivocally identified by HMBC NMR analysis.

Methyl 8- and 5-Nitro-1,4-Benzodioxane-2-Carboxylate / E. Armano, A. Giraudo, C. Morano, M. Pallavicini, C. Bolchi. - In: MOLBANK. - ISSN 1422-8599. - 2023:2(2023 Jun 06), pp. M1661.1-M1661.7. [10.3390/M1661]

Methyl 8- and 5-Nitro-1,4-Benzodioxane-2-Carboxylate

E. Armano
Primo
;
A. Giraudo
Secondo
;
C. Morano;M. Pallavicini
Penultimo
;
C. Bolchi
Ultimo
2023

Abstract

2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible to further synthetically useful conversions is the condensation of commercially available methyl 2,3-dibromopropionate with already suitably functionalized catechol. Here, we obtain methyl 8- and 5-nitro-1,4-benzodioxane-2-carboxylate by reaction of methyl 2,3-dibromopropionate with 3-nitrocatechol. After separation, the two positional isomers could be unequivocally identified by HMBC NMR analysis.
8-nitro-1,4-benzodioxane-2-carboxylate; 5-nitro-1,4-benzodioxane-2-carboxylate; HMBC NMR; regioisomers; structure elucidation;
Settore CHIM/08 - Chimica Farmaceutica
6-giu-2023
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/984488
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