Dihydrofuran ring opening in the reactions of 2,3-dihydrofuro[3,2-c]coumarin-3-one with arylhydrazines

作者：Kondratova N A; Solov'eva N P; Traven V F^*

来源：Russian Chemical Bulletin, 2010, 59(8): 1612-1620.

DOI：10.1007/s11172-010-0285-y

• furocoumarinones
• hydrazones
• tautomerism
• isomerization
• labeled nitrogen atom
• electronic absorption spectra

2,3-Dihydrofuro[3,2-c]coumarin-3-one reacts with arylhydrazines via two routes. The corresponding hydrazones are formed from arylhydrazines in alcohol and nitrophenylhydrazines in acetic acid or toluene. With phenylhydrazine and para-tolylhydrazine in toluene, 2,3-dihydrofuro[3,2-c]coumarin-3-one reacts unusually undergoing dihydrofuran ring opening and the formation of the corresponding 3-(2-imino-1-(2-arylhydrazinyl)ethylidene)-chromane-2,4-diones. The solvatochromic properties of the synthesized compounds were studied using electronic absorption spectra and quantum chemical calculations.

• 出版日期2010-8
• 单位北京化工大学