1,2,3,4-tetrahidro-4-fenilizokinolin-3-on, fenili zokinolinyum, ... -imidazolin-N-oksid ve 5-6-dihidro-4H-1,2,5 oksadiojin bileşiklerinin sentezleri ve özelliklerinin araştırılması.
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Date
1992-04-12
Authors
Coşkun, Necdet
Journal Title
Journal ISSN
Volume Title
Publisher
Uludağ Üniversitesi
Abstract
Tersiyer fenilasetamidler aynı kapta sodyum veya potasyum borhidrür beraberinde, karşılık gelen aromatik aldehid, amin ve arilasetil klorürden elde edildiler. Oluşan ürünler kurşun tetraasetat ile O-asetilmandelamid türevlerine dönüştürüldüler. Amidden O-asetilmandelamidi veren teaksiyon sadece aril halkasında elektron salan gruplara sahip olan amidlerle gerçekleştirildi. O-Asetilmandelamid türevleri, proton veya Lewis asidleri ile 1,2,3,4-tetrahidroizokinolin-3-on'lara dönüştürüldüler. N,N-Disübstitüe fenilasetamidler oksidleyici olarak kurşun tetraasetat asetik asid trifluorasetik asid karışımında kullanılarak doğrudan l,2,3,4-tetrahidroizokinolin-3-on lara dönüştürüldüler. A -Imidazolin-N-oksidler, karşılık gelen aromatik Schiff bazları ile syn-2-bromoasetofenon oksimin reaksiyonundan elde edildiler. Bazı örneklerde 5,6-dihidro-4H-1,2,5-oksadiazinler de yan ürün olarak izole edildiler.
Tertiary phenylacetamides w ere prepared from the corresponding aromatic aldehydes, amines and arylacetyl chlorides in the presence of sodium or potassium borohydride, as a on pot reaction. The resulting compounds were converted into O-acetylmandelamide derivatives with lead tetraacetate. The reaction from amide to O-acetilmandelamide proceeds only with amides having electrondonating groups at the aryl ring. O-Acetylmandelanri.de derivatives were converted into 1,2,3,4-tetrahydroisoquinolin-3-ones in the presence of protonic or Levzis acids. Some of the N,N-disubstituted phenylacetamides were converted directly into 1,2,3,4-tetrahydroisoquinolin-3-ones in the presence of lead tetraacetate as oxidant in the mixture of acetic acid and trifluoroacetic acid. A -Imidazolin-N-oxides were prepared by the reaction of corresponding aromatic Schiff bases with syn-2-bromoacetophenone oxime. 5,6-Dihydro-4H-l,2,5-oxadiazines were also isolated as byproduct in some instances.
Tertiary phenylacetamides w ere prepared from the corresponding aromatic aldehydes, amines and arylacetyl chlorides in the presence of sodium or potassium borohydride, as a on pot reaction. The resulting compounds were converted into O-acetylmandelamide derivatives with lead tetraacetate. The reaction from amide to O-acetilmandelamide proceeds only with amides having electrondonating groups at the aryl ring. O-Acetylmandelanri.de derivatives were converted into 1,2,3,4-tetrahydroisoquinolin-3-ones in the presence of protonic or Levzis acids. Some of the N,N-disubstituted phenylacetamides were converted directly into 1,2,3,4-tetrahydroisoquinolin-3-ones in the presence of lead tetraacetate as oxidant in the mixture of acetic acid and trifluoroacetic acid. A -Imidazolin-N-oxides were prepared by the reaction of corresponding aromatic Schiff bases with syn-2-bromoacetophenone oxime. 5,6-Dihydro-4H-l,2,5-oxadiazines were also isolated as byproduct in some instances.
Description
Keywords
Heterosiklik bileşikler, Heterocyclic compounds, İminyum tuzları, Iminium salts
Citation
Coşkun, N. (1992). 1,2,3,4-tetrahidro-4-fenilizokinolin-3-on, fenili zokinolinyum, ... -imidazolin-N-oksid ve 5-6-dihidro-4H-1,2,5 oksadiojin bileşiklerinin sentezleri ve özelliklerinin araştırılması. Yayınlanmamış doktora tezi. Uludağ Üniversitesi Fen Bilimleri Enstitüsü.