Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides

Yeliz FATURACI; Necdet COŞKUN

Makale detayları

Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides

Yazarlar:

Yeliz FATURACI | Necdet COŞKUN

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2012 Vol.36 Issue 5, pp.749-758

Belge Tipi:

Makale

Yayın Tarihi:

4/2012

Belge Dili:

Türkçe

Document ID (Org No.):

2000727561

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

Itaconic anhydride reacts with aryl amines to give a  substituent controlled equilibrium mixture of regioisomeric  (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids.  Electron-donating groups favor nucleophilic attack on C-5 carbonyl,  while the presence of electron-withdrawing groups enhances the bias  for attack on C-2 carbonyl.  The treatment of (Z)-2-methyl- and  (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl2-Et3N in  THF provided the corresponding maleimides in high yields while under  the same conditions the maleic anhydride aryl amine addition products  gave predominately the corresponding  3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent  dependent ratio.

 

Itaconic anhydride reacts with aryl amines to give a  substituent controlled equilibrium mixture of regioisomeric  (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids.  Electron-donating groups favor nucleophilic attack on C-5 carbonyl,  while the presence of electron-withdrawing groups enhances the bias  for attack on C-2 carbonyl.  The treatment of (Z)-2-methyl- and  (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl2-Et3N in  THF provided the corresponding maleimides in high yields while under  the same conditions the maleic anhydride aryl amine addition products  gave predominately the corresponding  3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent  dependent ratio.

Makale detayları

Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides

Yazarlar: Yeliz FATURACI | Necdet COŞKUN

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2012 Vol.36 Issue 5, pp.749-758

Belge Tipi: Makale

Yayın Tarihi: 4/2012

Belge Dili: Türkçe

Document ID (Org No.): 2000727561

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Yeliz FATURACI | Necdet COŞKUN

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2012 Vol.36 Issue 5, pp.749-758

Belge Tipi:

Makale

Yayın Tarihi:

4/2012

Belge Dili:

Türkçe

Document ID (Org No.):

2000727561

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527