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

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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 CDCl3 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.

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Acknowledgments

The authors are thankful to CONICYT for financial assistance through FONDECYT Postdoctoral Fellowship # 3150474.

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  1. Universidad de Chile, Santiago, Chile

    Thirumal Yempala & Bruce K. Cassels

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  1. Thirumal Yempala
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  2. Bruce K. Cassels
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Correspondence to Thirumal Yempala.

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Yempala, T., Cassels, B.K. Synthesis, scope, 1H and 13C spectral assignments of isomeric dibenzofuran carboxaldehydes. Res Chem Intermed 43, 1291–1299 (2017). https://doi.org/10.1007/s11164-016-2698-1

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