1993 Fiscal Year Final Research Report Summary
Synthesis of Polycyclic Organosilicon Compounds and Their Biological Evaluation
| Project/Area Number |
04671313
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Science University of Tokyo |
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Principal Investigator |
HOSHINO Osamu Science Univ.of Tokyo, Faculty of Phamaceutical Sciences Professor, 薬学部, 教授 (40084420)
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| Co-Investigator(Kenkyū-buntansha) |
OGASAWARA Hiromichi Science Univ.of Tokyo, Faculty of Phamaceutical Sciences Research Assistant, 助手 (10177107)
HARA Hiroshi Science Univ.of Tokyo, Faculty of Phamaceutical Sciences Assistant Professor, 助教授 (50096715)
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| Project Period (FY) |
1992 – 1993
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| Keywords | 5-Silacyclotriveratrylene / 6-Acy1-2-silatetralin / 2-Silaoctahydroanthracene Derivative / Dibenzo[de, g]-1-siladecalin / Dibenzo[d, f]-1-silacyclononane / 1-(omicron-bromoarylmethy1)-2-silatetralin / intramolecular Friedel-Crafts type reaction / aryl radical-mediated intramolecular cyclization |
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| Research Abstract |
(1)Synthesis of 5-Silacyclotriveratrylenes : Dilithiation of 1,2-bis (6-bromoveratryl)-4,5-dimethoxybenzene with butyllithium in THF followed by treatment with dichlorosilanes afforded the title compounds in good yields.
(2)Synthesis of 6-Acyl-2-silatetralins : Reaction of 2-silatetralin with acid anhydrides or acid chloride in the presence of aluminum chloride in dichloromethane at ambient temperature proceeded at the 6-position 2-silatetralin to afford exclusively the title compounds in good yields.
(3)Synthesis of 2-silaoctahydroanthracene Derivatives : Although direct cyclization of the ketoacids obtained by reaction of 2-silatetralin with succinic or phthalic acid anhydride in a manner to that described in 2) failed, cyclization of the the acid chlorides derived by reduction of a carbonyl to a methylene groups by means of intramolecular Friedel-Crafts type reaction led to the corresponding cyclized products in fair to good yield.
(4)Synthesis of Dibenzo[de, g]-1-siladecalins and Dibenzo[d, f]-1-silacyclononanes : The arylradical-mediated intramolecular cyclization of 1-(omicron-bromoarylmethyl)-2-silatetralins with tributyltin hydride in boiling benzene containing a catalytic amount of azobisisobutyronitrile furnished the title compounds in fair to good yields.
(5)Biological Evaluation for the Compounds : Biological evaluation is now under way.
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