Synthesis, scope, 1H and 13C spectral assignments of isomeric dibenzofuran carboxaldehydes

doi:10.1007/s11164-016-2698-1

Paper

Synthesis, scope, 1H and 13C spectral assignments of isomeric dibenzofuran carboxaldehydes

Published Mar 1, 2017 · Thirumal Yempala, B. Cassels

Research on Chemical Intermediates

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Abstract

Two isomeric dibenzofuran carboxaldehydes, namely 2-methoxydibenzo[b,d]furan-1-carbaldehyde (4) and 2-methoxydibenzo[b,d]furan-3-carbaldehyde (5), were synthesized. Formylation of 2-methoxydibenzo[b,d]furan (3) with α,α-dichloromethyl methyl ether and tin(IV) chloride gave a mixture of aldehydes 4 and 5 in 95 % yield and in a 35:65 ratio. Their ^1H and ^13C NMR spectral signals were not sufficiently resolved in CDCl_3 solution to achieve their complete assignment, but this was possible in DMSO-d _6 with the help of 2D-NMR techniques: NOESY for ^1H–^1H interactions and HSQC and HMQC experiments for ^1H–^13C correlations. These aldehydes were used in the synthesis of novel β-phenylethylamines and NBOMe derivatives, which are undergoing biological evaluation.

Study Snapshot

Two isomeric dibenzofuran carboxaldehydes were synthesized in a 35:65 ratio, with their use in the synthesis of novel -phenylethylamines and NBOMe derivatives under investigation.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis, scope, 1H and 13C spectral assignments of isomeric dibenzofuran carboxaldehydes

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