Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine |
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| Authors: | Kiyofumi Inamoto Mika Katsuno Yukari Arai Takao Sakamoto |
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| Affiliation: | a Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-ku, Sendai 980-8578, Japan
b Tohoku University 21st Century COE Program ‘Comprehensive Research and Education Center for Planning of Drug Development and Clinical Evaluation’, Sendai 980-8578, Japan |
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| Abstract: | Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described. |
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| Keywords: | Palladium Amination Hydrazone Indazole Benzoisoxazole Nigellicine |
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