1,2,3,4 - tetrahidroizokinolin türevlerinin sentezleri ve bazı araürünlerin kimyasal özelliklerinin araştırılması
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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.