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Novel Thermal and Microwave-Assisted Facile Route to naphthalen-2(1H)-ones via an Oxidative Alkoxylation-Ring-Opening Protocol

Novel Thermal and Microwave-Assisted Facile Route to naphthalen-2(1H)-ones via an Oxidative Alkoxylation-Ring-Opening Protocol

Chrysanthi Dolka, Kristof Van Hecke, Luc Van Meervelt, Petros G Tsoungas, Erik V Van der Eycken, George Varvounis

Org Lett. 2009 Jul 16;11(14):2964-7.

PMID: 19586060

Abstract:

Several novel 1,1-disubstituted-8-hydroxynaphthalen-2(1H)-ones have been efficiently synthesized via a two-step sequence from 2-hydroxy-1-naphthaldehyde oxime. The methodology involves oxidative ring closure and alkoxylation to 3a-alkoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-ones, followed by thermal ring-opening. Both thermal and microwave irradiation conditions were used. A novel one-pot reaction of oxime to 8-isopropoxynaphthalene-1,7-diol using microwave irradiation is also reported.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7470099	2-Hydroxy-1-naphthaldehyde oxime		7470-09-9	Price

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