Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives

M. Emin ŞENGÜL; Abdullah Menzek And Metin BALCI; Metin BALCI

Makale detayları

Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives

Yazarlar:

M. Emin ŞENGÜL | Abdullah Menzek And Metin BALCI | Metin BALCI

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2006 Vol.30 Issue 2, pp.131-138

Belge Tipi:

Makale

Yayın Tarihi:

1/2006

Belge Dili:

Türkçe

Document ID (Org No.):

2000728912

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

1,4-Dihydroxy-7,8-dihydro-5H-benzo[a]cycloheptene-5,9(6H)-  dione (7) was synthesised from hydroquinone and glutaric acid chloride  via an acylation reaction.  The reaction of dione (7) with bromine  followed by treatment with NEt3 gave homonaphthazarin 8 as well as  the brominated derivatives 9 and 10.  Reduction of  1,4-dimethoxy-7,8-dihydro-5H-benzo[a]cycloheptene-5,9(6H)-dione (16)  with LiAlH4 gave 2 isomeric alcohols, 17 and 18.  Reaction of these  alcohols with SOCl2 followed by HCl elimination with NEt3 afforded  dimethoxybenzocycloheptatriene 19 as the sole product.  For the  synthesis of the isomeric cycloheptatriene 20, the double bond in 19  was isomerised with KOt-Bu.

 

1,4-Dihydroxy-7,8-dihydro-5H-benzo[a]cycloheptene-5,9(6H)-  dione (7) was synthesised from hydroquinone and glutaric acid chloride  via an acylation reaction.  The reaction of dione (7) with bromine  followed by treatment with NEt3 gave homonaphthazarin 8 as well as  the brominated derivatives 9 and 10.  Reduction of  1,4-dimethoxy-7,8-dihydro-5H-benzo[a]cycloheptene-5,9(6H)-dione (16)  with LiAlH4 gave 2 isomeric alcohols, 17 and 18.  Reaction of these  alcohols with SOCl2 followed by HCl elimination with NEt3 afforded  dimethoxybenzocycloheptatriene 19 as the sole product.  For the  synthesis of the isomeric cycloheptatriene 20, the double bond in 19  was isomerised with KOt-Bu.

Makale detayları

Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives

Yazarlar: M. Emin ŞENGÜL | Abdullah Menzek And Metin BALCI | Metin BALCI

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2006 Vol.30 Issue 2, pp.131-138

Belge Tipi: Makale

Yayın Tarihi: 1/2006

Belge Dili: Türkçe

Document ID (Org No.): 2000728912

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

M. Emin ŞENGÜL | Abdullah Menzek And Metin BALCI | Metin BALCI

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2006 Vol.30 Issue 2, pp.131-138

Belge Tipi:

Makale

Yayın Tarihi:

1/2006

Belge Dili:

Türkçe

Document ID (Org No.):

2000728912

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527