54028-72-7Relevant academic research and scientific papers
Atropisomerism in the 2,3,4,5-Tetrahydro-1 H -1,5-benzodiazepine Nucleus: Effects of Central Chirality at C3 on the N-Mesylation Reaction
Tabata, Hidetsugu,Tsuji, Yuka,Yoneda, Tetsuya,Tasaka, Tomohiko,Oshitari, Tetsuta,Takahashi, Hideyo,Natsugari, Hideaki
, p. 2141 - 2146 (2018)
The mesylation reaction of the 1,3-dimethyl-2,3,4,5-tetrahydro-1 H -1,5-benzodiazepine nucleus was investigated in detail. Two diastereomers (A and B) of 5-mesyl-1,3-dimethyl-2,3,4,5-tetrahydro-1 H -1,5-benzodiazepines, originating from chirality at C3 and at the Ar-N(SO 2) axis were formed, among which isomers of the derivative with a methyl group at C6 (R = CH 3) were separable at room temperature. A and B had chair-like and boat-like conformations, respectively, in which the C3-methyl group adopts a pseudoequatorial arrangement. Furthermore, A and B were shown to be the thermodynamically and kinetically controlled products, respectively.
