Details

Autor(en) / Beteiligte

• Yempala, Thirumal
• Cassels, Bruce K.

Titel

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

Ist Teil von

• Research on chemical intermediates, 2017, Vol.43 (3), p.1291-1299

Ort / Verlag

Dordrecht: Springer Netherlands

Erscheinungsjahr

2017

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 1 H and 13 C 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 1 H– 1 H interactions and HSQC and HMQC experiments for 1 H– 13 C correlations. These aldehydes were used in the synthesis of novel β -phenylethylamines and NBOMe derivatives, which are undergoing biological evaluation.