学位論文

Ugi 反応によるヘテロ環を含むアズレンアミド誘導体の合成

FACILE SYNTHESIS OF AZULENE AMIDE DERIVATIVES WITH HETEROCYCLIC RESIDUES USING UGI REACTION

jpn

2008-03-24

Not Applicable (or Unknown)

2008-03-24

修士(工学)

工学研究科物質化学専攻; 指導教授: 中村暢男

Many synthetic research reports on heterocyclic compounds by Ugi reaction have appeared in recent years. Starting from 3-isocyanoguaiazulene (3-isocyano-7-isopropyl-1,4-dimethylazulene), there were performed our synthetic studies by Ugi reaction on a series of amide derivatives consisting of an aminoguaiazulene and heterocyclic acid residues. Thus, Ugi four-component condensation (Ugi 4CC) of aldehyde, 4-chloro-2-nitrobenzoic acid, ethyl glycinate hydrochloride, and 3-isocyanoguaiazulene in methanol under basic conditions afforded the corresponding Ugi products, which were reductively cyclized to benzodiazepine derivatives. Use of thiosalicylic acid instead of the nitrobenzoic acid under similar conditions resulted in formation of benzothiazepine derivatives. Further, the Ugi 4CC of aldehydes, chloroacetic acid, amines, and 3-isocyanoguaiazulene, and the Ugi 3CC reactions of aldehydes, β-alanine, and 3-isocyanoguaiazulene gave the isomeric azulenoid β-lactams, respectively

Thesis