Synthesis of a Bicyclic Diamine Derived from Kemp's Acid

Synthesis of rigidified flavin–guanidinium ion conjugates and investigation of their photocatalytic properties

“…The synthesis of the potential photocatalysts 1 and 2 , consisting of the flavin chromophore, the guanidinium substrate binding site and a Kemp’s acid derived rigid linker, starts from Kemp’s acid anhydride ( 5 ) [ 50 – 52 ]. The anhydride 5 was allowed to react with previously prepared flavins 4 and 8 [ 21 ] in the presence of DMAP as catalyst.…”

“…The flavin salts 4 [10-(2-aminoethyl)-3,7,8-trimethylbenzo[g]pteridine-2,4(3 H ,10 H )-dione] and 8 [3-(2-aminoethyl)-10-(2-methoxyethyl)-7,8-dimethylbenzo[g]pteridine-2,4(3 H ,10 H )-dione], Kemp’s acid anhydride 5 (1,5,7-trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carboxylic acid) and mono Boc-protected guanidine were prepared by known methods [ 21 , 50 – 52 ]. All other chemicals were purchased from commercial suppliers, checked by 1 H NMR spectrometry and then used as received.…”