Synthesis and Application of Fluoroazulenes
Project/Area Number |
09640648
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Organic chemistry
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Research Institution | Nihon University |
Principal Investigator |
YASUNAMI Masafumi College of Engineering, Professor, 工学部, 教授 (50004346)
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Project Period (FY) |
1997 – 1998
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Project Status |
Completed (Fiscal Year 1998)
|
Budget Amount *help |
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1998: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1997: ¥2,800,000 (Direct Cost: ¥2,800,000)
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Keywords | Alkylazulene / Fluoroazulene / Electrophilic Substitution / Nucleophilic Substitution / Aminoazulene / Diazonium Salt / Physiologically Active Compound / Functional Compound / トリアルキルアズレン / 5(6)-アミノアズレン / 6-フルオロアズレン / 5-フルオロアズレン |
Research Abstract |
Recently, we started to systematic synthetic studies of fluoroazulenes by electrophilic substitution reaction of azulene and some alkylazulenes. Present project is objected to the further extension of this synthetic studies of fluoroazule es and consisted from following two parts. 1) Synthesis of new alkylazulenes and their fluorination with N-fluoropyridiunium salts. 2) Synthetic studies of fluoroazulenes by nucleophilic substitujon reaction of azulene diazonium salts by fluorides. Four kind of new dialkylazulenes and five kind of trialkylazulenes were synthesized by the application of the Hafner's methyl introduction reaction with methyllithium to the alkylazulenes which were synthesized by the applications of our azulene synthetic method. The fluorination reaction of new dialkylazulenes with N-fluoropyridinum salt gave fluoroazulenes in 40-50% yields. On the other hand, the reaction of trialkky azulenes gave mainly insoluble precipitates which were assumed to be CT-complexes. The structural elucidation of the complexes and recovery of azulenes from thecomplexes were now studied. Synthetic methods of aminoazulenes and diazotization method of the aminoazulenes were established. However, nuclehophilic substituion of the diazonium salt by decomposition in the presence of fluoride gave only trace amount of fluoroazulenes. Studies of physiological activities and functional properties of synthesized new fluoroazulenes are now in progress.
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Report
(3 results)
Research Products
(12 results)
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[Publications] F.Shimoma, H.Kusaka, K.Wada, H.Azami, M.Yasunami, T.Suzuki, H.Hagiwara, and M.Ando: "A Novel Synthetic Method of the (3aalpha, 8aalpha) -Ethy18b-Hydroxy-6beta-methyl-2-oxooctahydro-2H-cyclohepta [b] furan-3alpha-carboxylate and its Chemical Transformation. Possible common Synthetic Intermediates for Pseudoguaianolides, 4,5-Secopseudo-guaianolides, Guaianolides, 4,5-Secoguaianolides, and Octalactins." J.Org.Chem.63(4). 920-929 (1998)
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[Publications] H.Wakabayashi, T.Kurihara, K.Shindo, M.Tsukada, Paw-Wang Yang, M.Yasunami, and (the late) T.Nozoe: "Synthesis and Reactivities of 1,5-and 1,7-Azulenequinone Derivatives. A Highly Convenient, One-Pot Synthesis of 3-Bromo-1,5-and-1,7-Azulenequinones by Bromination of Azulene." J.Chinese Chem.Soc.45. 391-400 (1998)
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[Publications] N.Morita, M.Hurita, H.Saito, M.Kinjo, S.Ito, T.Asao, M.Ueno, T.Sato, A.Tajiri, and Masafumi Yasunami.: "Reactivity of (2,4-cycloheptadiene-1,6-dione) Fe) CO) _3 : Synthesis of hinokitiol and (7,8-diphenylheptatriafulvalene-1,6-quinone) Fe (CO) _3" J.Org.Metal.Chem.570. 265-274 (1998)
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「研究成果報告書概要(欧文)」より
Related Report
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