Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(04): 455-464
DOI: 10.1055/s-0033-1340484
DOI: 10.1055/s-0033-1340484
paper
Reductive Alkylation of Hydrazine Derivatives with α-Picoline-Borane and Its Applications to the Syntheses of Useful Compounds Related to Active Pharmaceutical Ingredients
Further Information
Publication History
Received: 12 September 2013
Accepted after revision: 03 December 2013
Publication Date:
02 January 2014 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Hydrazine and its Derivatives . In Kirk-Othmer Encylopedia Chemical Technology . 4th ed., Vol. 13. Kirk RE, Othmer DF. Wiley; New York: 1995
- 2 Bold G, Fassler A, Capraro H-G, Cozens R, Klimkait T, Lazdins J, Mestan J, Poncioni B, Rosel J, Stover D, Tintelnot-Blomley M, Acemoglu F, Ucci-Stoll K, Wyss D, Lang M. J. Med. Chem. 1988; 41: 3387
- 3 The Japanese Pharmacopeia, 16th edition: http://www.pmda.go.jp/english/pharmacopoeia/online.html.
- 4 Gardner TS, Rutherford Lee J, Fells E, Wenis E. US Patent US2908688, 1959 ; Chem. Abstr. 1962, 56, 25114.
- 5a Tsubouchi H, Sasaki H, Itotani M, Haraguchi Y, Miyamura S, Matsumoto M, Hashizume H, Tomishige T, Kawasaki M, Ohguro K, Shimada T, Hasegawa T, Tanaka K, Takemura I. Patent WO2005-042542, 2005 ; Chem. Abstr. 2005, 142, 463728.
- 5b Kobayashi K, Nishiyama T, Nakade M. JP11302280, 1999 ; Chem. Abstr. 1999, 131, 299442.
- 5c Fukuzaki K. Japanese Patent JP05201990, 1993 ; Chem. Abstr. 1994, 120, 13446.
- 5d Kametani T, Kigasawa K, Hiragi M, Wagatsuma N, Uryu T, Araki K. J. Med. Chem. 1973; 16: 301
- 5e Kametani T, Kigasawa K, Hiragi M, Wagatsuma N, Kuama O, Uryu T. Chem. Pharm. Bull. 1976; 24: 2563
- 6 Selective double N-alkylation of hydrazine derivatives through their dianions has been reported: Bredihin A, Maeorg U. Tetrahedron 2008; 64: 6788
- 7a Perdichia D, Licandro E, Maiorana S, Baldoli C, Giannini C. Tetrahedron 2003; 59: 7733
- 7b Ragnarsson U. Chem. Soc. Rev. 2001; 30: 205
- 7c Arterburn JB, Rao KV, Ramdas R, Dible BR. Org. Lett. 2001; 3: 1351
- 7d Brosse N, Pinto MF, Bodiguel J, Jamart-Gregoire B. J. Org. Chem. 2001; 66: 2869
- 7e Brosse N, Pinto M, Jamart-Gregoire B. J. Org. Chem. 2000; 65: 4370
- 7f Baruah B, Dutta MP, Boruah A, Prajapati D, Sandhu JS. Synlett 1999; 409
- 7g Katritzky AR, Qiu G, Yang B. J. Org. Chem. 1997; 62: 8210
- 7h Maeorg U, Grehn L, Ragnarsson U. Angew. Chem., Int. Ed.. Engl. 1996; 35: 2626
- 8 Mizufune H, Yamamoto H, Nakamura M, Miki S. Tetrahedron 2008; 64: 6275
- 9a Terada T, Fujimoto K, Nomura M, Yamashita J, Wierzba K, Yamazaki R, Shibata J, Sugimoto Y, Yamada Y, Kobunai T, Takeda S, Minami Y, Yoshida K. J. Med. Chem. 1993; 36: 1689
- 9b Nelson SF, Weisman GR. Tetrahedron Lett. 1973; 26: 2321
- 10 Kawase Y, Yamagishi T, Kutsuma T, Zhibao H, Yamamoto Y, Kimura T, Nakata T, Kataoka T, Yokomatsu T. Org. Process Res. Dev. 2012; 16: 495
- 11 Kawase Y, Yamagishi T, Kutsuma T, Ueda K, Iwakuma T, Nakata T, Yokomatsu T. Heterocycles 2009; 78: 463
- 12 Kawase Y, Yamagishi T, Kutsuma T, Kataoka T, Ueda K, Iwakuma T, Nakata T, Yokomatsu T. Synthesis 2010; 1673
- 13 For a previous report on general reductive amination of carbonyl compounds with amines using α-PicBH3, see: Sato S, Sakamoto T, Miyazawa E, Kikugawa Y. Tetrahedron 2004; 60: 7899
- 14 For a report on α-PicBH3-mediated reductive alkylation of 2,4-dinitrophenylhydrazine supported on silica gel with aldehydes, see: Uchiyama S, Inaba Y, Matsumoto M, Suzuki G. Anal. Chem. 2009; 81: 485
- 15 Although acid catalysts are effective to accelerate the formation of hydrazone, excess amount of acids may inhibit the formation of hydrazone due to protonation of hydrazine moiety. Therefore, we added hydrochloric acid or oxalic acid in the steps for the formation of hydrazone and for the reduction separately.
- 16 The sequential double alkylation with cyclohexane-carbaldehyde and n-hexanal failed under the conditions.
- 17 Okawa T, Kanazawa Y, Yamasaki T, Furukawa M. Synthesis 1987; 183
- 18 For the synthesis of the hydrochloride salt, see ref. 7a.