Reaction of 1,4-phthalazinedione with furfural: Formation of the [5,6]benza-3a,7a-diazaindane system via an unusual skeletal rearrangement

Organic Letters

Volumn 4, Issue 5, 2002, Pages 773-775

  Amarasekara, Ananda S ^a,b   Chandrasekara, Susantha ^a  

^a UNIVERSITY OF COLOMBO   (Sri Lanka)

^b UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042810927     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017256+     Document Type: Article

References (25)

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15. Experimental procedure for compound 7a: Phathalahydrazide (324 mg, 2.0 tnmol) and furfuraldehyde (576 mmol, 6.0 mmol) were dissolved in 30 mL of methylene chloride, and to this mixture was added lead tetracetate (886 mg, 4 mmol) in small portions during a period of 10 min, while the solution was kept under vigorous stirring at room temperature. The solution was further stirred for 20 min. The resulting mixture was passed through a short coloumn of neutral alumina (2 × 5 cm) and then the column was washed with 100 mL of methylene chloride. Combined eluent was concentrated under reduced pressure and the residue was recrystallized from ethyl acetate to give 7a as a white powder, 312 mg, 64% yield, mp 221-3 °C.
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