Title:
α-ペルフルオロアルキルアミン化合物のラジカル合成に用いることのできるチオカルボニルスルファニル基を有する新規化合物
Document Type and Number:
Japanese Patent JP4869595
Kind Code:
B2
Abstract:
Halogenated S-alpha-aminoalkyl dithiocarboxylate, dithiocarbamate or di- or tri-thiocarbonate compounds (I) are new. Also new are S-gamma-aminoalkyl thiocarbamylsulfanyl compounds (II) and 1,2-diamines (VIII). Thiocarbonylsulfanyl compounds of formula (I) and their salts are new. Z1 = alkyl, acyl, aryl, aralkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, ORa, SRa or NRiRj; Ra = alkyl, haloalkyl, alkenyl, alkynyl, acyl, aralkyl, aralkenyl, aralkynyl, carbocyclyl, heterocyclyl, polymer chain or -CRbRc-P(O)(ORd)(ORe); Rb, Rc = H, alkyl, perfluoroalkyl, carbocyclyl, heterocyclyl, NO2, NCO, CN, Rf, SO3Rf, SRf, NRfRg, COORf, OCORf, CONRfRg or -NCORfRg; or CRbRc = CO, CS, carbocycle or heterocycle; Rf, Rg = alkyl, alkenyl, alkynyl, cycloalkenyl, cycloalkynyl, aryl (optionally fused with a heterocycle), alkaryl, aralkyl or heteroaryl; Rd, Re = as for Rf; or Rd + Re = 2-4C hydrocarbon chain (optionally interrupted by O, S or NRh); Rh = as for Rf; Ri, Rj = alkyl, haloalkyl, alkenyl, alkynyl, acyl, ester group, aryl, aralkyl, aralkenyl, aralkynyl, carbocyclyl or heterocyclyl; or Ri + Rj = 2-4C hydrocarbon chain (optionally interrupted by O, S or NRh); Z2, Z3 = H, alkyl, aryl, cycloalkyl or an electron attracting group, provided that at least one of Z2 and Z3 is a group inducing an electron attractive effect to the N atom to which it is bonded; Z4 = H, alkyl or cycloalkyl; RF = halogen (preferably F), haloalkyl, poly- or perhalogenated aryl, RA-CF2-, RA-CF2CF2-, RA-CF2CF(CF3)-, CF3-CF(RA)- or )CF3)RA-; RA = alkyl, acyl, aryl, aralkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl. Independent claims are also included for: (1) The preparation of (I); (2) New thiocarbonylsulfanyl compounds of formula (II); (3) The preparation of (II); (4) The preparation of amines of formula (IV) by reduction of (II); (5) The preparation of unsaturated amines of formula (V) by subjecting (II; R7 = H) to elimination reaction; (6) The preparation of thiocarbonylsulfanyl compounds of formula (VI) by radical addition reaction of (II) with an olefin; (7) The preparation of amino-aldehydes of formula (VII) by subjecting (II; R6 and R8 = H and acyloxy) to conversion, in the presence of an organic or mineral acid; (8) The specific new compounds (conversion products of (II)) N-(3-(2-oxo-pyrrolidin-1-yl)-1-trifluoromethyl-allyl)-acetamide, N-(4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-trifluoromethyl-butyl)-acetamide, O-ethyl S-(1-(5-(1-acetylamino-2,2,2-trifluoroethyl)-2-oxo-(1,3)-dioxolan-4-ylmethyl)-2,2-diethoxy-ethyl)-dithiocarbonate, N-(1-(5-bromo-1-methanesulfonyl-2,3-dihydro-1H-indol-3-ylmethyl)-2,2,2-trifluoroethyl)-acetamide and N-(3,3-dimethoxy-1-trifluoromethyl-propyl)-acetamide; (9) New diamines of formula (VIII); and (10) The preparation of (VIII). Z5 - Z8 = H, halo, alkyl, haloalkyl, alkenyl, alkynyl, acyl, aryl, aralkyl, aralkenyl, aralkynyl, carbocyclyl, heterocyclyl, polymer chain, -(CH2)m-ORk, -CH(ORk)(ORl). -(CH2)m-SRk, -(CH2)m-SO3Rk, -(CH2)m-NO2, -(CH2)m-CN, -(CH2)m-Rk, -(CH2)m-PO(ORkRl)2, -(CH2)m-SiRkRlRm, -(CH2)m-COORk, -(CH2)m-NCORk or -(CH2)m-NRkRl; or pairs of groups Z5 - Z8 may together form one or more carbocyclic or heterocyclic rings; Rk, Rl, Rm = alkyl, acyl, aryl, alkenyl, alkynyl, aralkyl, alkaryl, aralkynyl, carbocyclyl or heterocyclyl; m = 1 or more; Z9 - Z12 = as for Z5 - Z8.
Inventors:
Samil monkey
Fabian Gagos
Lucy Tournier
Fabian Gagos
Lucy Tournier
Application Number:
JP2004535602A
Publication Date:
February 08, 2012
Filing Date:
September 11, 2003
Export Citation:
Assignee:
Center National de la Cherche Sientifique (Se en Els)
International Classes:
C07C329/16; C07C67/293; C07C67/297; C07C69/63; C07C69/78; C07C231/12; C07C233/13; C07C233/18; C07C233/36; C07C233/69; C07C233/78; C07C327/36; C07C329/18; C07D207/27; C07D209/12; C07D209/14; C07D209/48; C07D317/36; C07D339/06; C07F7/08; C07F9/40; C07C233/31; C07D207/26
Domestic Patent References:
| JP2003522816A | ||||
| JP2002508409A | ||||
| JP2002512653A | ||||
| JP3291265A |
Foreign References:
| US3450818 | ||||
| US3190882 |
Other References:
Phosphorus, Sulfur and Silicon and the Related Elements,1995年,105(1-4),p.33-44
Zhurnal Organicheskoi Khimii,1989年,25(4),p.759-764
Acta Facultatis Rerum Naturalium Universitatis Comenianae, Chimia,1968年,No.13,p.53-64
Zhurnal Organicheskoi Khimii,1989年,25(4),p.759-764
Acta Facultatis Rerum Naturalium Universitatis Comenianae, Chimia,1968年,No.13,p.53-64
Attorney, Agent or Firm:
Axis International Patent Business Corporation