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

Sabrina Baptista Ferreira; Daniel Tadeu Gomes Gonzaga; Fernando de Carvalho da Silva; Katia Gomes de Lima Araújo; Vitor Francisco Ferreira

doi:10.1055/s-0030-1260778

LETTER

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

Sabrina Baptista Ferreira^a, Daniel Tadeu Gomes Gonzaga^a, Fernando de Carvalho da Silva^a, Katia Gomes de Lima Araújo^b, Vitor Francisco Ferreira*^a
^a Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, 24020-141 Niterói, Rio de Janeiro, Brazil
Fax: +55(21)26292362; e-Mail: cegvito@vm.uff.br;
^b Universidade Federal Fluminense, Faculdade de Farmácia, Departamento de Bromatologia, CEP 24241-000, Niterói, RJ, Brasil

Abstract

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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.

Key words

β-lapachone - ortho-quinone methide - microwave - isomerization

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References

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