Efficient approaches to S-alkyl-N-alkylisothioureas: syntheses of histamine H3 antagonist clobenpropit and its analogues

…, T Kurihara, A Yamatodani, S Harusawa

Index: Yoneyama, Hiroki; Shimoda, Ayako; Araki, Lisa; Hatano, Kouta; Sakamoto, Yasuhiko; Kurihara, Takushi; Yamatodani, Atsushi; Harusawa, Shinya Journal of Organic Chemistry, 2008 , vol. 73, # 6 p. 2096 - 2104

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Citation Number: 12

Abstract

S-Alkyl-N-alkylisothioureas were efficiently synthesized via synthetic approach (A) using 3- phenylpropionyl isothiocyanate (PPI). The utility of the approach was proved by the syntheses of clobenpropit, a potent histamine H3 antagonist, and its analogues. Alternatively, clobenpropit could be prepared via intramolecular amide cleavage (B) with use of 2-nitrophenylacetyl isothiocyanate (NPAI).