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

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.

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

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.

Kaynakça

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Kaynak Göster

Bibtex @ { tbtkchem142558, journal = {Turkish Journal of Chemistry}, issn = {1300-0527}, eissn = {1303-6130}, address = {}, publisher = {TÜBİTAK}, year = {2006}, volume = {30}, pages = {131 - 138}, doi = {}, title = {Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives}, key = {cite}, author = {Şengül, M. Emin and Balcı, Abdullah Menzek And Metin and Balcı, Metin} }
APA Şengül, M , Balcı, A , Balcı, M . (2006). Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives . Turkish Journal of Chemistry , 30 (2) , 131-138 .
MLA Şengül, M , Balcı, A , Balcı, M . "Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives" . Turkish Journal of Chemistry 30 (2006 ): 131-138 <
Chicago Şengül, M , Balcı, A , Balcı, M . "Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives". Turkish Journal of Chemistry 30 (2006 ): 131-138
RIS TY - JOUR T1 - Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives AU - M. Emin Şengül , Abdullah Menzek And Metin Balcı , Metin Balcı Y1 - 2006 PY - 2006 N1 - DO - T2 - Turkish Journal of Chemistry JF - Journal JO - JOR SP - 131 EP - 138 VL - 30 IS - 2 SN - 1300-0527-1303-6130 M3 - UR - Y2 - 2021 ER -
EndNote %0 Turkish Journal of Chemistry Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives %A M. Emin Şengül , Abdullah Menzek And Metin Balcı , Metin Balcı %T Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives %D 2006 %J Turkish Journal of Chemistry %P 1300-0527-1303-6130 %V 30 %N 2 %R %U
ISNAD Şengül, M. Emin , Balcı, Abdullah Menzek And Metin , Balcı, Metin . "Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives". Turkish Journal of Chemistry 30 / 2 (Şubat 2006): 131-138 .
AMA Şengül M , Balcı A , Balcı M . Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives. Turk J Chem. 2006; 30(2): 131-138.
Vancouver Şengül M , Balcı A , Balcı M . Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives. Turkish Journal of Chemistry. 2006; 30(2): 131-138.
IEEE M. Şengül , A. Balcı ve M. Balcı , "Construction of a Homonaphthazarin Skeleton and Synthesis of Hydroquinone-annelated Cycloheptatriene Derivatives", Turkish Journal of Chemistry, c. 30, sayı. 2, ss. 131-138, Şub. 2006