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Journals / 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
Pages
131–138
Publication Date
2006-02-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

For the synthesis of the isomeric cycloheptatriene 20, the double bond in 19 was isomerised with KOt-Bu.

📌 3 Key Takeaways

🎯
Objective & Hypothesis: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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Key Findings & Data: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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Conclusion & Impact:For the synthesis of the isomeric cycloheptatriene 20, the double bond in 19 was isomerised with KOt-Bu.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Naphthazarin · homonaphthazarin · benzocycloheptatriene

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.

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.

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Cite This Article

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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References (10)

  1. R.H. Thomson, “Naturally Occurring Quinones III, Recent Advances”, Chapman and Hall: London, pp. 127-343, 1987.
  2. M. Kikuchi, Yuki Gosei Kagaku Kyokaishi 48, 157-63 (1990). R.H. Thompson, “Naturally Occurring Quinones”, 2nd ed. Academic Press: London and New York, 1971.
  3. V.P. Papageorgiou, A.N. Assimopoulou, E.A. Couladouros, D. Hepworth and K.C. Nicolaou, Angew. Chem. Int. Ed. 38, 270-300 (1999).
  4. T. Ogasawara, K. Chiba and M. Tada, Phytochemistry 33, 1095-1098 (1993).
  5. A.F.M.F. Hasan, T. Furmoto, S. Begum and H. Fukui, Phytochemistry, 58, 1225-1228 (2001).
  6. D.B. Bruce, A.J.S. Sorrie and R.H. Thomson, J. Chem. Soc. 2403-2406 (1953).
  7. A.J.S. Sorrie and R.H. Thomson, J. Chem. Soc. 2233-2238 (1955).
  8. A.J.S. Sorrie and R.H. Thomson, J. Chem. Soc. 2238-2243 (1955).
  9. J.F. Garden and R.H. Thomson, J. Chem. Soc. 2851-2854 (1957).
  10. T. Horaguchi, K. Tanemure and T. Suzuki, J. Heterocyclic Chem. 39-43 (1988).