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Lewis Acid‐Catalyzed or Base‐Promoted Regioselective Cycloisomerization of N‐Imidoyl‐o‐alkynylanilines for Synthesis of N‐Imidoyl‐(1 H)‐indoles and 4‐Alkylidene‐3,4‐dihydroquinazolines

Corresponding Author

totani@rs.tus.ac.jp

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

Research Center for Chirality, Research Institute for Science & Technology, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271Search for more papers by this author

Xue Jiang

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

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Kinryo Cho

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

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Rino Araki

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

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Noriki Kutsumura

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

International Institute for Integrative Sleep Medicine (WPI‐IIIS), University of Tsukuba, 1‐1‐1 Tennodai, Tsukuba, Ibaraki 305‐8577, Japan

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Takao Saito

Corresponding Author

tsaito@rs.kagu.tus.ac.jp

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

Takashi Otani

Corresponding Author

totani@rs.tus.ac.jp

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

Xue Jiang

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

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Kinryo Cho

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

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Rino Araki

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

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Noriki Kutsumura

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

International Institute for Integrative Sleep Medicine (WPI‐IIIS), University of Tsukuba, 1‐1‐1 Tennodai, Tsukuba, Ibaraki 305‐8577, Japan

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Takao Saito

Corresponding Author

tsaito@rs.kagu.tus.ac.jp

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku‐ku, Tokyo 162‐8601, Japan, Fax: (+81)‐3‐5261‐4631; phone: (+81)‐3‐3262‐4271

First published: 13 April 2015

https://doi.org/10.1002/adsc.201401186

Citations: 18

Abstract

Product selectivity control for the synthesis of imidoylindoles and 4‐alkylidenedihydroquinazolines from N‐imidoyl‐o‐alkynylanilines via silver triflate‐catalyzed cycloisomerization or tetrabutylammonium fluoride‐promoted cyclization is described. The product selectivity depends mainly on the catalyst/promoter used, and on the substituents on the alkyne and amidine functions of the substrates.