TY - JOUR
T1 - Ammonium Salt-Accelerated Hydrazinolysis of Unactivated Amides
T2 - Mechanistic Investigation and Application to a Microwave Flow Process
AU - Noshita, Megumi
AU - Shimizu, Yuhei
AU - Morimoto, Hiroyuki
AU - Akai, Shuji
AU - Hamashima, Yoshitaka
AU - Ohneda, Noriyuki
AU - Odajima, Hiromichi
AU - Ohshima, Takashi
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas (JSPS KAKENHI Grant JP15H05846 in Middle Molecular Strategy for T.O.) from JSPS, Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS) (Grant JP17am0101091) from AMED, and the Takasago Award in Synthetic Organic Chemistry, Japan (for H.M.). M.N. and Y.S. thank JSPS for Research Fellowships for Young Scientists. The computations were carried out using the computer resources offered under the category of General Projects by the Research Institute for Information Technology at Kyushu University.
PY - 2019/4/19
Y1 - 2019/4/19
N2 - A study of ammonium salt-accelerated hydrazinolysis of unactivated amides is described. We first studied the reaction mechanism by kinetic experiments and DFT calculations and found that cooperation of the hydrazinium salt and hydrazine is important for promoting the cleavage of unactivated amides. Next, we applied the reaction to a microwave flow process, and the amine products were isolated on a multigram scale.
AB - A study of ammonium salt-accelerated hydrazinolysis of unactivated amides is described. We first studied the reaction mechanism by kinetic experiments and DFT calculations and found that cooperation of the hydrazinium salt and hydrazine is important for promoting the cleavage of unactivated amides. Next, we applied the reaction to a microwave flow process, and the amine products were isolated on a multigram scale.
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U2 - 10.1021/acs.oprd.8b00424
DO - 10.1021/acs.oprd.8b00424
M3 - Article
AN - SCOPUS:85064595130
VL - 23
SP - 588
EP - 594
JO - Organic Process Research and Development
JF - Organic Process Research and Development
SN - 1083-6160
IS - 4
ER -