| Project/Area Number |
62550612
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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 |
有機工業化学
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| Research Institution | Osaka University |
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Principal Investigator |
KOMATSU Mitsuo Osaka University, Faculty of Eng, Associate Professor, 工学部, 助教授 (60029197)
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| Project Period (FY) |
1987 – 1988
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| Project Status |
Completed (Fiscal Year 1988)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1988: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1987: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | Functionalized cyclopropane / Functionalized heterocumulene / Heterocyclic synthesis / Azadiene / Imidazolinone / 多官能三員環 / シクロプロピルイソシアナート / オチシフト |
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| Research Abstract |
Creations of new synthetic reagents and reactions for multi-functionalization of heterocycles or synthesis of new heterocycles are of great importance to develop new or better utilities of heterocycles. Thus development of functionalized three-membered ring compounds as novel and versatile synthons for heterocyclces was studied, where release of large strain energy of the ring is a key tep.
Synthetic methods of new halocyclopropylheterocumulenes have been established and were applied to heterocyclic synthesis. For example, treatment of a dibromocyclopropylurea derivative with MeONa in MeOH gave a ring-opened product which easily recyclized under acidic conditions to an imidazolinone. Starting with a semicarbazide derivative, a triazolidinone having bromovinyl substituent could be synthesized. Furthermore, it was found that nitrogen substituted mono- and dihalocyclopropane derivatves are easily ring-opened to form azadienes upon treatment with a base. Cycloaddtion of the in-situ generated azadiene was also confirmed. Hence these halocyclopropyl derivatives are good precursors of azadienes which are highly effective reagents for heterocyclic synthesis.
As results, the functionalized cyclopropanes were found to be useful synthetic reagents for heterocycles where a three carbon unit is incorporated to ring systems.
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