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Synthesis 2014; 46(04): 455-464
DOI: 10.1055/s-0033-1340484
paper
© Georg Thieme Verlag Stuttgart · New York

Reductive Alkylation of Hydrazine Derivatives with α-Picoline-Borane and Its Applications to the Syntheses of Useful Compounds Related to Active Pharmaceutical­ Ingredients

Yasushi Kawase
a   School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Fax: +81(42)6763239   Email: yokomatu@toyaku.ac.jp
,
Takehiro Yamagishi
a   School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Fax: +81(42)6763239   Email: yokomatu@toyaku.ac.jp
,
Jun-ya Kato
a   School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Fax: +81(42)6763239   Email: yokomatu@toyaku.ac.jp
,
Teruo Kutsuma
a   School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Fax: +81(42)6763239   Email: yokomatu@toyaku.ac.jp
,
Tadashi Kataoka
b   Yokohama College of Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama, Kanagawa 245-0066, Japan
,
Takeo Iwakuma
c   Fine Chemical Department, Chemicrea Incorporation, Quattro Muromachi Bldg. 9F., 4-1-6, Nihonbashi Muromachi, Chuo-ku, Tokyo 103-0022, Japan
,
Tsutomu Yokomatsu*
a   School of Pharmacy, Tokyo University of Pharmacy & Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   Fax: +81(42)6763239   Email: yokomatu@toyaku.ac.jp
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Further Information

Publication History

Received: 12 September 2013

Accepted after revision: 03 December 2013

Publication Date:
02 January 2014 (online)

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Abstract

An efficient method for the direct reductive alkylation of hydrazine derivatives with α-picoline-borane has been developed to synthesize a variety of N-alkylhydrazine derivatives. This method provided N,N-dialkylhydrazine derivatives and N-monoalkylhydrazine derivatives upon fine-tuning of the substrates and the reagent equivalency in a one-pot manner. The method was applied to the synthesis of active pharmaceutical ingredients of therapeutic drugs such as isocarboxazid.

Key words

alkylation - hydrazones - reduction - hydrazines - α-picoline-borane

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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