2013 Fiscal Year Final Research Report
Novel Construction of Fused Pyridine Alkaloid Skeletons via Hetero Diels-Alder Reaction of Isotellurazoles
| Project/Area Number |
23550039
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Iwate University |
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Principal Investigator |
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| Project Period (FY) |
2011 – 2013
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| Keywords | イソテルラゾール / ヘテロ環化付加 / 多置換ピリジン / Friedel-Crafts環化 / 縮環ピリジン類 |
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| Research Abstract |
Hetero Diels-Alder reaction of isotellurazoles are recognized as a novel method for the regioselective synthesis of substituted pyridines, and we just attempted the expansion of the new methodology to the short-step synthesis of fused pyridine alkaloid skeletons. After an enormous efforts of our research work, we just attempted and succeeded in the short-step synthesis of fused pyridine alkaloid skeletons by using our original hetero Diels-Alder reaction of isotellurazoles and suitably designed electron-deficient acetylenic dienophiles as the important key step. Furthermore, we could find the subsequent Friedel-Crafts ring closure of the resulting pyridine ring bearing an aryl and ester groups on the suitable positions, and a convenient and short-step synthesis of a few fused pyridine alkaloid skeletons, i.e. b- and d-carbolines, 1- and 4-azafluorenones, 1-azaphenanthrenes, 1-azaanthraquinones, were finally achieved under a rather mild reaction conditions through our methodology.
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Research Products
(15 results)
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[Presentation] Synthesis of 2, 3-Dihydro-1, 2, 4-thiadiazoles and 1, 2, 4-Oxadiazoles through Oxidative Cyclization of 1, 3-Thiaza-1, 3-butadienss2013
Author(s)
Isogami Megumi, Kazuaki Shimada, and Toshinobu Korenaga
Organizer
International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan (平成25年度化学系学協会東北大会および日本化学会東北支部 70 周年記念国際会議)
Place of Presentation
仙台市, 東北大学川内キャンパス
Year and Date
20130928-30
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