Carbohydrate Research p. 34 - 42 (2000)
Update date:2022-08-04
Topics:
Awad, Laila F.
Reaction of the oxidation product of L-ascorbic acid, dehydro-L-ascorbic acid, with o-phenylenediamine, followed by 2,4,6-trichlorophenylhydrazine (3) afforded 3-[1-(2,4,6-trichlorophenylhydrazono)-L-threo-2,3,4-trihydroxybut-1- yl]quinoxalin-2(1H)one (4), whose structure was deduced from studying its periodate oxidation, which gave the glyoxal derivative 3-[1-(2,4,6- trichlorophenylhydrazono)glyoxal-1-yl]quinoxalin-2(1H)one (5) that upon reduction afforded 3-[1-(2,4,6-trichlorophenylhydrazono)-2-hydroxyethy-1- yl]quinoxalin-2(1H)one (6). The reaction of 5 with 3 afforded the bishydrazone 3-[1,2-bis(2,4,6-trichlorophenylhydrazono)glyoxal-1- yl]quinoxalin-2(1H)one. The reaction of 5 with acetic anhydride in pyridine afforded the 2,3-dihydrofuro[2,3-b]quinoxaline derivative 2-acetoxy-3-[2- acetyl-2-(2,4,6-trichlorophenyl)hydrazono)]-2,3-dihydrofuro[2,3- b]quinoxaline. Acetylation of 4 with acetic anhydride in pyridine afforded the acyclic diacetate intermediate 3-[3,4-di-O-acetyl-2-deoxy-1-(2,4,6- trichlorophenylhydrazono)but-2-en-1-yl]quinoxalin-2(1H)one (12), which was also obtained from the reaction of 4 with boiling acetic anhydride. Compound 12 rearranged under the reaction conditions to give the pyrazole derivatives 3-[5-(acetoxymethyl)-1-(2,4,6-trichlorophenyl)pyrazol-3-yl]quinoxalin- 2(1H)one (14) and 2-acetoxy-3-[5-(acetoxymethyl)-1-(2,4,6- trichlorophenyl)pyrazol-3-yl)]quinoxaline (15), as well as the 2,3- dihydrofuro[2,3-b]quinoxaline derivative 2-(2-acetoxyethen-2-yl)-3-[2-(2,4,6- trichlorophenyl)hydrazono]-2,3-dihydrofuro[2,3-b]quinoxaline. Acetylation of 3-[5-(hydroxymethyl)-1-(2,4,6-trichlorophenyl)pyrazol-3-yl]quinoxalin- 2(1H)one (16) with acetic anhydride in pyridine or 12 with boiling acetic anhydride afforded 15 and 16, respectively. Treatment of 4 with diluted sodium hydroxide afforded the pyrazolo[2,3-b]quinoxaline (flavazole) derivative 1-(2,4,6-trichlorophenyl)-3-(L-threo-glycerol-1-yl)pyrazolo[2,3- b]quinoxaline whose acetylation afforded the acetyl derivative 3-(2,3,4-tri- O-acetyl-L-threo-glycerol-1-yl)-1-(2,4,6-trichlorophenyl)pyrazolo[2,3- b]quinoxaline. The assigned structures were based on spectral analysis. The activity of compound 4 against hepatitis B virus has been studied. (C) 2000 Elsevier Science Ltd.
View MoreSHANGHAI T&W PHARMACEUTICAL CO., LTD.
website:http://www.trustwe.com
Contact:+86-21-61551611
Address:601, No. 1, 2277 Nong, Zu Chongzhi Road, Zhangjiang Hightech. Park, Pudong
Anhui Eapearl Chemical Co., Ltd.
Contact:86-562-5858458
Address:358 South Huaihe Road
Contact:+86-25-83719363
Address:106-7 Chunnan Rd, Chunxi Town, Gaochun, Nanjing, China
GUANGZHOU MEDCAN PHARMATECH LTD
website:http://www.gzmedcan.com
Contact:+86-20-82519649
Address:Building J,Room 101,1 JiangtashanRd,Guang Zhou Science City,Guang Zhou ,China
Chongqing maohuan Chemicals Co., Ltd
website:http://www.bschem.com
Contact:+86 13996103726
Address:Chongqing Nan'an District Tu Town
Doi:10.1021/ic00128a027
(1995)Doi:10.1021/acs.joc.5b01824
(2015)Doi:10.1021/jo01273a052
(1968)Doi:10.1021/jo00127a055
(1995)Doi:10.1007/BF00696931
(1995)Doi:10.1016/0040-4039(95)02221-X
(1996)