Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)H)H)-ones in a palladium catalyzed Sonogashira cross-coupling reaction

Malose Jack MPHAHLELE; Felix Adetunji OYEYIOLA

Makale detayları

Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)H)H)-ones in a palladium catalyzed Sonogashira cross-coupling reaction

Yazarlar:

Malose Jack MPHAHLELE | Felix Adetunji OYEYIOLA

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2015 Vol.39 Issue 6, pp.1216-1231

Belge Tipi:

Makale

Yayın Tarihi:

12/2015

Belge Dili:

İngilizce

Document ID (Org No.):

2000726728

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

Pd/C-PPh33_{3}--CuI catalyzed Sonogashira cross-coupling of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)H)H)-ones with phenyl acetylene or 3-butyn-1-ol afforded the corresponding 8-alkynylated quinolin-4(1H)H)H)-one derivatives, exclusively. Double carbo-substitution to afford the 6,8-dialkynyl derivatives was observed when PdCl22_{2}(PPh3)23)2_{3})_{2} was used as Pd(0) source. The monoalkynylated derivatives were, in turn, subjected to PdCl22_{2} in acetonitrile under reflux to afford either the corresponding 2,4-diaryl-8-bromopyrrolo[3,2,1-\textit{ij}]quinolinones or the 8-(4-hydroxybutanoyl)-substituted quinolinone derivatives, exclusively. Suzuki--Miyaura cross-coupling of the 2-aryl-6-bromo-8-(alkynyl)quinolin-4-ones afforded the 2,4,8-trisubstituted pyrrolo[3,2,1-\textit{ij}]quinolin-6-ones.

 

Pd/C-PPh33_{3}--CuI catalyzed Sonogashira cross-coupling of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)H)H)-ones with phenyl acetylene or 3-butyn-1-ol afforded the corresponding 8-alkynylated quinolin-4(1H)H)H)-one derivatives, exclusively. Double carbo-substitution to afford the 6,8-dialkynyl derivatives was observed when PdCl22_{2}(PPh3)23)2_{3})_{2} was used as Pd(0) source. The monoalkynylated derivatives were, in turn, subjected to PdCl22_{2} in acetonitrile under reflux to afford either the corresponding 2,4-diaryl-8-bromopyrrolo[3,2,1-\textit{ij}]quinolinones or the 8-(4-hydroxybutanoyl)-substituted quinolinone derivatives, exclusively. Suzuki--Miyaura cross-coupling of the 2-aryl-6-bromo-8-(alkynyl)quinolin-4-ones afforded the 2,4,8-trisubstituted pyrrolo[3,2,1-\textit{ij}]quinolin-6-ones.

Makale detayları

Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)H)H)-ones in a palladium catalyzed Sonogashira cross-coupling reaction

Yazarlar: Malose Jack MPHAHLELE | Felix Adetunji OYEYIOLA

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2015 Vol.39 Issue 6, pp.1216-1231

Belge Tipi: Makale

Yayın Tarihi: 12/2015

Belge Dili: İngilizce

Document ID (Org No.): 2000726728

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Malose Jack MPHAHLELE | Felix Adetunji OYEYIOLA

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2015 Vol.39 Issue 6, pp.1216-1231

Belge Tipi:

Makale

Yayın Tarihi:

12/2015

Belge Dili:

İngilizce

Document ID (Org No.):

2000726728

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527