1992 Fiscal Year Final Research Report Summary
Development of Novel Organic Fine Chemicals based on Polycycles
| Project/Area Number |
02555174
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| Research Category |
Grant-in-Aid for Developmental Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Nagoya University |
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Principal Investigator |
EGUCHI Shoji Nagoya Univ., Fac. of Eng., Prof., 工学部, 教授 (50023106)
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| Co-Investigator(Kenkyū-buntansha) |
田中 鎮也 住友化学工業(株)宝塚総合研究所, 農業科学研究所, 主席研究員
KAWASAKI K Idemitsu Kosan Cent.Res.Int., G.Leader, 光・電子材料研究室, 室長
OKANO T Nagoya Univ., Fac. of Eng., Assi,Prof., 工学部, 助手 (90194373)
OHNO M Nagoya Univ., Fac. of Eng., Asso.Prof., 工学部, 助教授 (50072682)
MINAMOTO K Nagoya Univ., Fac. of Eng., Prof., 工学部, 教授 (50023106)
TANAKA S Sumitomo Chemical Inst.Agr.Sci., H.Scintst.
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| Project Period (FY) |
1990 – 1992
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| Keywords | Azahomoadamant-4-ene / Nitrone / Iminophosphorane / Quinazoline alkaloid / Cyclonucleoside / Reductive ring-enlargement / 2, 2'-Anhydrothymine / Trifluoromethyl group |
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| Research Abstract |
In this project, design and synthesis of some selected carbo- and heteropolycycles have been carried out in order to develop novel organic fine chemicals for industrial use based on polycycles like adamantane. The results can be summarized as follows :
1) A bridge-imine, 4-azahomoadamant-4-ene obtainable readily from adamantane was converted to the corresponding N-oxide, i.e., a novel bridged nitrone, which was shown to be useful intermediate for synthesis of homoadamantano [4,5] fused heterocycles such as isooxazolidines, isooxazolines, and pyrroles etc.
2) A short-step synthesis of quinazoline alkaloids, Rutecarpine and Tryptanthrin has been developed via intramolecular aza-Wittig methodology. A novel route to polyazamacrocycles has been developed via quinazolinone-annelation of lactams, followed by reductive ring-enlargement.
3) A cyclonucleoside, 2,2'-anhydrothymine derivative was shown to be useful inter-mediate for biologically important 3'-substituted arabinonucleosides.
4) A facile synthesis of beta-chloro-beta-trifluoromethyl DELTA^<alpha,beta>-carbonyl compounds has been developed by using transition metal-induced coupling reaction. Also a novel route to indole skeletons via [4+2] cycloaddition reaction of acetyl pyrrole derivatives has been developed. These compounds are expected as useful synthetic blocks for bioactive compounds.
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