ChemInform Abstract: SYNTHESIS AND STUDY OF THE NEUROTROPIC ACTION OF 2‐SUBSTITUTED METHANOISOINDOLES

A new synthesis of methanoisoindoles

“…However, we failed to reproduce this procedure. Kobayashi et al [7] also failed to obtain compound ΙΙ under the conditions described in [4]. The authors [7] developed a four-step procedure for the synthesis of ΙΙ via reaction of aromatic amine with 3-(diethoxymethyl)bicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde (adduct of cyclopentadiene with 4,4-diethoxybut-2-ynal), followed by reduction of the products to amines and cyclization of the latter to the corresponding methanoisoindoles.…”

“…Lebedev et al [4] described a procedure for the synthesis of 4-aryl-4-azatricyclo[5.2.1.0 2,6 ]deca-2,5,8-trienes ΙΙ in 62-65% yield by reaction of amines with cyclopentadiene adduct Ι with cis/trans-isomeric 2,5-dimethoxy-2,5-dihydrofurans in glacial acetic acid at 70-100°C (Scheme 1). However, we failed to reproduce this procedure.…”

“…Some isoindole derivatives were found to exhibit antihypertensive, antidiabetic, and antibacterial activity [3,4]. Polymeric composite materials based on isoindoles and methanoisoindoles are used in optoelectronics as fluorescent sensors and laser dyes [5,6].…”