Method of producing nitroguanidine- and nitroenamine...

Details Method of producing nitroguanidine- and nitroenamine... Method of producing nitroguanidine- and nitroenamine...

C - Chemistry, Metallurgy

07

D

C07D 417/06 (2006.01) C07C 257/22 (2006.01) C07C 261/00 (2006.01) C07C 277/08 (2006.01) C07D 213/38 (2006.01) C07D 213/40 (2006.01) C07D 213/61 (2006.01) C07D 277/28 (2006.01) C07D 277/36 (2006.01) C07D 307/14 (2006.01) C07D 401/06 (2006.01) C07C 279/36 (2006.01)

Patent

CA 2369404

Method of producing compounds of formula (I), wherein R1 is hydrogen or C1-C4- alkyl; R2 is hydrogen, C1-C8-alkyl, C3-C6-cycloalkyl, or a radical -N(R3)R4; or R2 and R6 together are -CH2-CH2-S-; R3 and R4 are hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl or a radical -CH2B; R6 is hydrogen, C1-C8-alkyl, aryl or benzyl; or R3 and R6 together are -CH2-CH2-, -CH2-CH2-CH2-, -CH2-O-CH2-, -CH2-S-CH2- or -CH2-N(R5)-CH2-; X is CH-CN; CH-NO2 or N-NO2; A is an optionally substituted, aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical; and B is optionally substituted phenyl, 3-pyridyl or thiazolyl; characterised in that a compound of formula (II), wherein R2, R6 and X have the same significance as given above in formula (I), is reacted in the presence of a phase transfer catalyst and a base with a compound of formula (III), wherein A and R1 have the same significance as given above in formula (I) and Q is a leaving group.

L'invention concerne un procédé de fabrication de composés correspondant à la formule (I), dans laquelle R¿1? est hydrogène ou alkyle C¿1?-C¿4?; R¿2? est hydrogène, alkyle C¿1?-C¿8?, cycloalkyle C¿3?-C¿6? ou un radical -N(R¿3?)R¿4?; ou R¿2? et R¿6? sont ensemble -CH¿2?-CH¿2?S-; R¿3? et R¿4? sont hydrogène, alkyle C¿1?-C¿4?, cycloalkyle C¿3?-C¿6? ou un radical -CH¿2?B; R¿6? est hydrogène, alkyle C¿1?-C¿8?, aryle ou benzyle; ou R¿3? et R¿6? sont ensemble -CH¿2?-CH¿2?-, -CH¿2?-CH¿2?-CH¿2?-, -CH¿2?-O-CH¿2?-, -CH¿2?-S-CH¿2?- ou -CH¿2?-N(R¿5?)-CH¿2?-; X est CH-CN; CH-NO¿2? ou N-NO¿2?; A est un radical hétérocyclique monocyclique ou bicyclique aromatique ou non-aromatique éventuellement substitué; B est un phényle, 3-pyridyle ou thiazolyle éventuellement substitué; caractérisée en ce que le composé de la formule (II), dans laquelle R¿2?, R¿6? et X ont les mêmes significations que dans la formule (I), réagit en présence d'un catalyseur à transfert de phase et d'une base avec un composé correspondant à la formule (III), dans laquelle A et R¿1? ont les mêmes significations que dans la formule (I) et Q est un groupe partant.

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