Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues

Ayşe TAN; Mustafa Zahrittin KAZANCIOĞLU; Derya AKTAŞ; Özlem GÜNDOĞDU; Ertan ŞAHİN; Nurhan HORASAN KİSHALI; Yunus KARA

Makale detayları

Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues

Yazarlar:

Ayşe TAN | Mustafa Zahrittin KAZANCIOĞLU | Derya AKTAŞ | Özlem GÜNDOĞDU | Ertan ŞAHİN | Nurhan HORASAN KİSHALI | Yunus KARA

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2014 Vol.38 Issue 4, pp.629-637

Belge Tipi:

Makale

Yayın Tarihi:

3/2014

Belge Dili:

Türkçe

Document ID (Org No.):

2000727134

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

Three new polysubstituted isoindole-1,3-diones were prepared from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione. The reaction of 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione with m-CPBA gave the corresponding epoxide. The triacetate derivative was obtained via cis-hydroxylation using OsO4, followed by acetylation. An aromatic derivative, a secondary reaction product, was also formed during the acetylation. Finally, a tricyclic derivative from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione was synthesized via dichloroketene addition under microwave irradiation. The exact structures of epoxide and tricyclic derivatives were determined by X-ray diffraction analysis.

 

Three new polysubstituted isoindole-1,3-diones were prepared from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione. The reaction of 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione with m-CPBA gave the corresponding epoxide. The triacetate derivative was obtained via cis-hydroxylation using OsO4, followed by acetylation. An aromatic derivative, a secondary reaction product, was also formed during the acetylation. Finally, a tricyclic derivative from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione was synthesized via dichloroketene addition under microwave irradiation. The exact structures of epoxide and tricyclic derivatives were determined by X-ray diffraction analysis.

Makale detayları

Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues

Yazarlar: Ayşe TAN | Mustafa Zahrittin KAZANCIOĞLU | Derya AKTAŞ | Özlem GÜNDOĞDU | Ertan ŞAHİN | Nurhan HORASAN KİSHALI | Yunus KARA

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2014 Vol.38 Issue 4, pp.629-637

Belge Tipi: Makale

Yayın Tarihi: 3/2014

Belge Dili: Türkçe

Document ID (Org No.): 2000727134

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Ayşe TAN | Mustafa Zahrittin KAZANCIOĞLU | Derya AKTAŞ | Özlem GÜNDOĞDU | Ertan ŞAHİN | Nurhan HORASAN KİSHALI | Yunus KARA

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2014 Vol.38 Issue 4, pp.629-637

Belge Tipi:

Makale

Yayın Tarihi:

3/2014

Belge Dili:

Türkçe

Document ID (Org No.):

2000727134

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527