1,2,3,4 - tetrahidroizokinolin türevlerinin sentezleri ve bazı araürünlerin kimyasal özelliklerinin araştırılması
Loading...
Files
Date
1990
Authors
Coşkun, Necdet
Journal Title
Journal ISSN
Volume Title
Publisher
Uludağ Üniversitesi
Abstract
Bu çalışmada, bazılarının antidepresan ve antiaritmik oldukları bilinen, 4-feni-l,2,3,4-tetrahidroizokinolinlerin sentezleri için etkin, yüksek verimli yöntemler geliştirilmiştir. Aromatik aldehidlerin alkilaminlerle İTaBH/ beraberinde aminolanmaları ilk defa indirgen ortamda aminoalkilleme olarak ge liştirilmiştir. Aminoalkilleme - haloasetofenonlarla, cl-halo- asetatlarla ve fv-haloasetamidlerle gerçekleştirilmiştir. Aminoalkilleme reaksiyonları sonucu elde edilen bileşikler, azot- içeren heterohalkalı bileşikler sentezlerinde kullanılmışlar dır. N-Alkil-N-benzil-2-aminoasetofenonlar çeşitli asidik or tamda 4-fenil-l,2-dihidroisokinolinlere dönüştürülmüş " ve bu maddelerin türlü indirgenler kullanılarak 4-fenil-l, 2,3,4-tetrahidroizokinolin sentezleri yapılmıştır.- 4-Penil-1.2-dihidroizökinolinlerin, 4-fenil-l, 2,,3,4-fcetra- hidroizokinolin ve 4-fenilizokinolinyum tuzu vermek üzere disproporsiyonlaşmaya uğradıkları kanıtlanmıştır. Bazı araürünlerin kimyasal özellikleri ve biyolojik aktif İlkleri test edilmiştir.
In this investigation, effective methods for the synthesis of 4-phenyl-l,2,3,4-tetrahidrosoquinolines v/ere discussed. Some of these compounds are known as antidepressants and antiarrithmics, The amination of the aromatic aldehydes with alkylamines in the presence of HaBH^ was improved as aminoalkylation. The amino- alkylation was realized with öC-haloasetophenones, <7C-haloece- tates and ot -haloacetamides. As a result of aminoalkylation reactions, a lot of intermediates were synthesised which are used in the synthesis of nitrogen containing heterocycles. The convertion of N-alkyl-M-bensyl-2-aminoacetophenones to 4-phenyl -1,2-dihydroisoquinolines in various acidic media and their reduction with various reducing agents, to 4-phenyl-l,2,3,4-tet- rahydroisoquinolines «ere reported. The disproportionation of 4-phenyl-l,2-dihydroisoquinolines to 4-phenyl-l,2,3,4-tetrahydroisoquinolines and fully aromatic isoquinolinium salts ^swere proved. The chemical properties and biological activities of some of the intermediates were investigated.
In this investigation, effective methods for the synthesis of 4-phenyl-l,2,3,4-tetrahidrosoquinolines v/ere discussed. Some of these compounds are known as antidepressants and antiarrithmics, The amination of the aromatic aldehydes with alkylamines in the presence of HaBH^ was improved as aminoalkylation. The amino- alkylation was realized with öC-haloasetophenones, <7C-haloece- tates and ot -haloacetamides. As a result of aminoalkylation reactions, a lot of intermediates were synthesised which are used in the synthesis of nitrogen containing heterocycles. The convertion of N-alkyl-M-bensyl-2-aminoacetophenones to 4-phenyl -1,2-dihydroisoquinolines in various acidic media and their reduction with various reducing agents, to 4-phenyl-l,2,3,4-tet- rahydroisoquinolines «ere reported. The disproportionation of 4-phenyl-l,2-dihydroisoquinolines to 4-phenyl-l,2,3,4-tetrahydroisoquinolines and fully aromatic isoquinolinium salts ^swere proved. The chemical properties and biological activities of some of the intermediates were investigated.
Description
Keywords
1,2,3,4-tetrahidroizokinolin, İzokinolin, 1,2,3,4-tetrahydroisoquinoline, Isoquinoline
Citation
Coşkun, N. (1990). 1,2,3,4 - tetrahidroizokinolin türevlerinin sentezleri ve bazı araürünlerin kimyasal özelliklerinin araştırılması. Yayınlanmamış yüksek lisans tezi. Uludağ Üniversitesi Fen Bilimleri Enstitüsü.