New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton

Çağatay DENGİZ; Metin BALCI

Makale detayları

New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton

Yazarlar:

Çağatay DENGİZ | Metin BALCI

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2013 Vol.37 Issue 2, pp.220-227

Belge Tipi:

Makale

Yayın Tarihi:

1/2013

Belge Dili:

Türkçe

Document ID (Org No.):

2000727451

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

We hereby report a new method for preparation of  3,4-dihydroquinolin-2(2H)-one starting from the methyl  2-(2-carboxyethyl)benzoic acid.  The acid functionality, adjacent to  the methylene, was regiospecifically converted to the desired methyl  ester and the remaining acid functionality was transferred into acyl  azide.  Curtius rearrangement of acyl azide followed by trapping with  aniline and alcohols provided the corresponding urea and urethane  derivatives.  Hydrolysis of methyl ester groups gave the acids.  Ring  closure in the presence of thionyl chloride resulted in the formation  of the 3,4-dihydroquinolin-2(2H)-one skeleton.

 

We hereby report a new method for preparation of  3,4-dihydroquinolin-2(2H)-one starting from the methyl  2-(2-carboxyethyl)benzoic acid.  The acid functionality, adjacent to  the methylene, was regiospecifically converted to the desired methyl  ester and the remaining acid functionality was transferred into acyl  azide.  Curtius rearrangement of acyl azide followed by trapping with  aniline and alcohols provided the corresponding urea and urethane  derivatives.  Hydrolysis of methyl ester groups gave the acids.  Ring  closure in the presence of thionyl chloride resulted in the formation  of the 3,4-dihydroquinolin-2(2H)-one skeleton.

Makale detayları

New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton

Yazarlar: Çağatay DENGİZ | Metin BALCI

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2013 Vol.37 Issue 2, pp.220-227

Belge Tipi: Makale

Yayın Tarihi: 1/2013

Belge Dili: Türkçe

Document ID (Org No.): 2000727451

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Çağatay DENGİZ | Metin BALCI

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2013 Vol.37 Issue 2, pp.220-227

Belge Tipi:

Makale

Yayın Tarihi:

1/2013

Belge Dili:

Türkçe

Document ID (Org No.):

2000727451

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527