Tetrahedron p. 1405 - 1408 (1982)
Update date:2022-08-02
Topics:
Su, T.-L.
Watanabe, K. A.
Fox, J. J.
The first intermolecular ring transformation of a uracil derivative into benzene system is reported.Treatment of 1,3-dimethyl-5-nitrouracil (1) with acetone in NaOMe/MeOH afforded 6-acetonyl-5,6-dihydro-1,3-dimethyl-5-nitrouracil (6) wich was converted into 4-nitroresorcinol (5) upon treatment with NaOEt/EtOH at reflux.Reaction of 1 with butanone gave two major products, 3-(5,6-dihydro-1,3-dimethyl-5-nitrouracil-6-yl)-butanone (7) and 1-(uracil-6-yl)butanone isomer (8).Prolonged treatment of 7 with NaOEt/EtOH afforded 4-methyl-6-nitro-resorcinol (9) whereas 8 was converted into 2-methyl-4-nitro-resorcinol (10).Treatment of 1 with diethyl acetonedicarboxylate in NaOEt/EtOH afforded diethyl-2-(5,6-dihydro-1,3-dimethyl-5-nitrouracil-6-yl)-acetonedicarboxylate (2).Prolonged treatment of 2 with NaOEt/EtOH at reflux afforded (5,6-dihydro-1,3-dimethyl-6-nitrouracil-6-yl)acetic acid (3).Apparently, 2 underwent a retroClaisen reaction to give 3.Reaction of 1 with ethyl acetoacetate in NaOEt/EtOH gave adduct isomers 4 which underwent transformation reaction to give eventually 6-nitroresorcinol (5).
View MoreZhengzhou Yuanli Biological Technology Co., Ltd.
Contact:+86-371-67897870/67897895
Address:No. 38, Qingyang Street, Zhengzhou, Henan, China
HANGZHOU PANYU CHEMICAL CO.,LIMITED
Contact:+86-571-86578491
Address:Rm 605, NO.1870 Binsheng Road,Binjiang Dist, Hangzhou, China
Jining tiansheng chemical co.,ltd.
Contact:+86-537-5158722
Address:ROOM 1011, BLOCK B, CUIDU INTERNATIOAL BUSINESS CENTER, JINING CITY, CHINA
Changzhou Medi-tech Bioscientific Co., Ltd.
Contact:86-519-83246372
Address:Number 115 Menghedadao Road, Changzhou, Jiangsu, China
Jiaxing Trustworthy Import And Export Co.,Ltd
Contact:+86-573-82030555
Address:Room 1202, Unit B, Charming plaza,No.1558 East Zhongshan Road , Jiaxing City, Zhejiang Province, China.
Doi:10.1021/ja302549c
(2012)Doi:10.1021/jacs.8b05043
(2018)Doi:10.1021/ja206644d
(2011)Doi:10.1134/S1070427211060255
(2011)Doi:10.1039/jr9500002108
(1950)Doi:10.1016/0022-328X(91)80086-Y
(1991)