Tetrahedron

Synthesis of porphyrinylamide and observation of N-methylation-induced trans–cis amide conformational alteration

M Matsumura, A Tanatani, T Kaneko, I Azumaya…

Index: Matsumura, Mio; Tanatani, Aya; Kaneko, Tomoyo; Azumaya, Isao; Masu, Hyuma; Hashizume, Daisuke; Kagechika, Hiroyuki; Muranaka, Atsuya; Uchiyama, Masanobu Tetrahedron, 2013 , vol. 69, # 51 p. 10927 - 10932

Full Text: HTML

Citation Number: 3

Abstract

Abstract We synthesized porphyrinylamide 4b and its N-methylated derivative 5b. Direct N- methylation of porphyrinylamides 4 proved unsuccessful, so 5b was obtained via N- methylation of 5-aminoporphyrin 10 with potassium hexamethyldisilazide. The secondary amide 4b exists in trans-amide form, while N-methylated amide 5b exists in the cis-amide form, both in solution and in the crystal. Thus, N-methylation of the amide bond of 4b ...