ŞALKONUN REDÜKSİYONUNDA BİR YAN ÜRÜN OLARAK YENİ BİR SİKLOPENTANOL

1,3-difenilpropanonlar üzerinde sürdürülmekte olan sentez çalışmalarının devamı olarak, potansiyel Santral Sinir Sistemi aktivitesine sahip olan 11,12-dihidro-10,5-(iminometano)-5H,10Hdibenzo[a,d]sikloooktenlerin total sentezinde anahtar araürün olan, 3-(3,4-dimetoksifenil)-l-(3-tolil)-2propenon, 3,4-dimetoksibenzaldehit ve 3-metilasetofenonun Claisen-Schmidt reaksiyonu ile elde edilmiştir. ikinci basamakta, şalkonun olefinik bağının redüksiyonu, Zn/asetik asit kullanılarak yapılmıştır. Her nekadar redüksiyon sırasında doymuş keton elde edilmiş olsa da, ana ürün siklodimerizasyonla oluşan yeni bir siklopentanoldür. Bu yeni bileşiğin kimyasal yapısı ve stereokimyası ID ve 2D NMR analizleri ile aydınlatılmıştır

Anahtar Kelimeler:

Propanonlar, şalkınlar, Claisen-Schmidt reaksiyonu, hidrodimerizasyon

A NEW CYCLOPENTANOL AS A SIDE PRODUCT IN THE REDUCTION OF THE CHALCONE

As a part of an ongoing study on the synthesis of 1,3-diphenylpropanones, as key intermediates in the total synthesis of 11,12-dihydro-10,5-(iminomethano)-5H,10H-dibenzo[a,d]cyclooctenes with potential Central Nervous System activity, 3-(3,4-dimethoxyphenyl)-l-(3-tolyl)-2-propenone is obtained by the Claisen-Schmidt reaction of 3,4-dimethoxybenzaldehyde and 3-methylacetophenone. At the second step, the reduction of the olefinic bond of chalcone was attempted by using Zn/acetic acid. Although the desired saturated ketone was obtained during this reduction, the major product was a new cyclopentanol, formed by cyclodimerization. The structure and the stereochemistry of this new compound was elucidated by ID and 2D NMR analyses

Keywords:

Propanones, chalcones, Claisen-Schmidt reaction, hydrodimerization,

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