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Dergiler / Turkish Journal of Chemistry / 2006 / Cilt: 30 - Sayı: 2

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

M. Emin ŞENGÜL
Abdullah Menzek And Metin BALCI
Metin BALCI
Sayfa
131–138
Yayın Tarihi
2006-02-01
DOI
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For the synthesis of the isomeric cycloheptatriene 20, the double bond in 19 was isomerised with KOt-Bu.

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Amaç & Hipotez: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.
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Temel Bulgular & Veri:The reaction of dione (7) with bromine followed by treatment with NEt3 gave homonaphthazarin 8 as well as the brominated derivatives 9 and 10.
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Sonuç & Katkı:For the synthesis of the isomeric cycloheptatriene 20, the double bond in 19 was isomerised with KOt-Bu.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Naphthazarin · homonaphthazarin · benzocycloheptatriene

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.

Abstract

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.

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Bu Makaleye Atıf Yap

ŞENGÜL, M. E., BALCI, A. M. A. M., BALCI, M. (2006). Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives. Turkish Journal of Chemistry, Cilt: 30 - Sayı: 2, 131–138. https://ajindex.com/articles/218012

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Kaynakça (10)

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