Synthesis of New o-Quinone Methides from β-Lapachone Analogues

Abstract In this work, we synthesized six new O-quinone methides from β-lapachone analogues by treating β-lapachone with acetone and a catalytic amount of iodine under thermal conditions and microwave irradiation. The yields of isolated O-quinone methides ranged from 20-80%. During the reactions, th...

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Bibliographic Details
Published in:Synlett 2011-07, Vol.2011 (11), p.1623-1625
Main Authors: Ferreira, Sabrina Baptista, Gonzaga, Daniel Tadeu, de Carvalho da Silva, Fernando, de Lima Araújo, Katia Gomes, Ferreira, Vitor Francisco
Format: Article
Language:English
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Summary:Abstract In this work, we synthesized six new O-quinone methides from β-lapachone analogues by treating β-lapachone with acetone and a catalytic amount of iodine under thermal conditions and microwave irradiation. The yields of isolated O-quinone methides ranged from 20-80%. During the reactions, the formation of α-pyran naphthoquinones was observed; the yields varied depending upon the substituent. The reactions using microwave irradiation were faster, but yields and selectivities did not change significantly.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1260778