Reaction ofN,N-bis(chloromethyl)amides withN,N′-diacylated alkene(arylene)diamines

Advances in 1,3,5-triazepines chemistry

“…The 1 H nuclear magnetic resonance (NMR) shis of 1,3,5-triazepanes with electron-withdrawing N-substituents 65 indicated the following proton resonance ranges: 3.2-3.8 ppm for NCH 2 -CH 2 N and 4.7-5.0 ppm for NCH 2 N fragments. Furthermore, triazepines 11 (R 1 ¼ H, NEt 2 ; R 2 , R 3 ¼ OMe, NEt 2 ) (Fig.…”

“…24,25 The cyclocondensation of diamines 43 (Scheme 7) with diethyl imino-dicarboxylate gave the corresponding 1,3,5triazepine-2,4-diones 44 in 48-53% yields, 89 whereas the reaction of 43 with N,N-bis(chloromethyl)amides afforded triazepanes 45. 65 The nonsymmetrical and benzo-fused analogs of 45 were prepared in a similar way. Substitution of both methylthio groups of thioimidates 46 with diamines 47 gave tetrahydrotriazepines 48 as the major products.…”

“…The reaction of 162 with nitromethane under similar conditions produced 163 (X ¼ H 2 ; R 1 ¼ NO 2 ; R 2 ¼ H) in a 44% yield (Scheme 43). 65 On treatment with ammonium uoride in water, 162 underwent seven-to six-membered ring contraction. 138…”