Molecules p. 13096 - 13110 (2013)
Update date:2022-08-04
Topics:
Maggio, Benedetta
Raffa, Demetrio
Raimondi, Maria Valeria
Daidone, Giuseppe
The compound 2-((1,3-dimethyl-1H-pyrazol-5-yl)(methyl)carbamoyl) benzenediazonium hydrogen sulfate (10) was reacted with copper sulfate and sodium chloride, in the presence of ascorbic acid as reducing agent, to afford a mixture of the chlorinated epimers 4′-chloro-2,2′,5′- trimethyl-2′,4′-dihydrospiro[isoindoline-1,3′-pyrazol]-3-one (18) and (19), the epimers 4′-hydroxy-2,2′,5′-trimethyl- 2′,4′-dihydrospiro[isoindoline-1,3′- pyrazol]-3-one (20) and (21), and N-(1,3-dimethyl-1H-pyrazol-5-yl)benzamide (22). Under the foregoing conditions, diazonium salt 10 affords neither the 2-chloro-N-(1,3-dimethyl- 1H-pyrazol-5-yl)-N-methylbenzamide (23) nor the tricyclic derivative 24, the classical products of the Sandmeyer and Pschorr reactions, respectively. Finally, by heating 20 at 210 °C the compound 1,3-dimethylisochromeno[4,3-c] pyrazol-5(1H)-one (24) was obtained. The transformation under the above conditions of 2-((4-chloro-3-methyl-1-phenyl- 1H-pyrazol-5-yl)(methyl)carbamoyl) benzendiazonium hydrogen sulphate (11) afforded 4′,4′-dichloro-2, 5′-dimethyl-2′-phenyl-2′,4′-dihydrospiro[isoindoline-1, 3′-pyrazol]-3-one (29) as the sole reaction product.
View MoreSHENZHEN PENGCHENG REDSTAR INDUSTRY CO.,LTD
Contact:+86-755-82412922
Address:Room 8066, East Block, Square City, Jiabin Road, Luohu District
FOSHAN NANHAI ZHONGNAN PHARMACEUTICAL FACTORY
Contact:0086-0757-85609331
Address:XIAHENGTIAN INDUSTRIAL ZONE,SHAYONG VILLAGE,LISHUI TOWN
website:http://www.fwdchem.com
Contact:86-21-54450828
Address:Room 802,Lotus Tower ,159 Tianzhou Road,Xuhui District,Shanghai
Beijing Century Richap Chemistry Co.,Ltd
Contact:+86- 010-64455497
Address:Guannan County, Lianyungang City, Jiangsu Province, China
Beijing Tianjia Chemical Science & Technology Co.,Ltd
Contact:86-0550-2392698
Address:No.388, Shiliang Road (East),
Doi:10.1016/S0968-0896(98)00082-0
(1998)Doi:10.1021/ja982329e
(1998)Doi:10.1002/ejoc.201700891
(2017)Doi:10.1055/s-1998-3141
(1998)Doi:10.1016/S0040-4039(01)87525-0
(1969)Doi:10.1016/S0960-894X(00)00474-1
(2000)