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Novel thermal and microwave-assisted facile route to naphthalen-2(1H)-ones via an oxidative alkoxylation-ring-opening protocol

Chrysanthi Dolka, Kristof Van Hecke UGent, Luc Van Meervelt, Petros G Tsoungas, Erik V Van der Eycken and George Varvounis (2009) ORGANIC LETTERS. 11(14). p.2964-2967
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
COUPLING REACTION, SUPPORTED IODOBENZENE DIACETATE, ORGANIC-SYNTHESIS, CESIUM FLUOROXYSULFATE, ACTIVATED AROMATIC SYSTEMS, PERI-CYCLIZATION, BETA-NAPHTHOL, FLUORINATION, ALUMINA, NAPHTHALENE
journal title
ORGANIC LETTERS
Org. Lett.
volume
11
issue
14
pages
2964 - 2967
Web of Science type
Article
Web of Science id
000268138800003
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
5.42 (2009)
JCR rank
4/57 (2009)
JCR quartile
1 (2009)
ISSN
1523-7060
DOI
10.1021/ol9008574
language
English
UGent publication?
no
classification
A1
id
2045714
handle
http://hdl.handle.net/1854/LU-2045714
date created
2012-02-27 11:02:18
date last changed
2018-01-29 12:12:31
@article{2045714,
  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.},
  author       = {Dolka, Chrysanthi and Van Hecke, Kristof and Van Meervelt, Luc and Tsoungas, Petros G and Van der Eycken, Erik V and Varvounis, George},
  issn         = {1523-7060},
  journal      = {ORGANIC LETTERS},
  keyword      = {COUPLING REACTION,SUPPORTED IODOBENZENE DIACETATE,ORGANIC-SYNTHESIS,CESIUM FLUOROXYSULFATE,ACTIVATED AROMATIC SYSTEMS,PERI-CYCLIZATION,BETA-NAPHTHOL,FLUORINATION,ALUMINA,NAPHTHALENE},
  language     = {eng},
  number       = {14},
  pages        = {2964--2967},
  title        = {Novel thermal and microwave-assisted facile route to naphthalen-2(1H)-ones via an oxidative alkoxylation-ring-opening protocol},
  url          = {http://dx.doi.org/10.1021/ol9008574},
  volume       = {11},
  year         = {2009},
}

Chicago
Dolka, Chrysanthi, Kristof Van Hecke, Luc Van Meervelt, Petros G Tsoungas, Erik V Van der Eycken, and George Varvounis. 2009. “Novel Thermal and Microwave-assisted Facile Route to naphthalen-2(1H)-ones via an Oxidative Alkoxylation-ring-opening Protocol.” Organic Letters 11 (14): 2964–2967.
APA
Dolka, C., Van Hecke, K., Van Meervelt, L., Tsoungas, P. G., Van der Eycken, E. V., & Varvounis, G. (2009). Novel thermal and microwave-assisted facile route to naphthalen-2(1H)-ones via an oxidative alkoxylation-ring-opening protocol. ORGANIC LETTERS, 11(14), 2964–2967.
Vancouver
1.
Dolka C, Van Hecke K, Van Meervelt L, Tsoungas PG, Van der Eycken EV, Varvounis G. Novel thermal and microwave-assisted facile route to naphthalen-2(1H)-ones via an oxidative alkoxylation-ring-opening protocol. ORGANIC LETTERS. 2009;11(14):2964–7.
MLA
Dolka, Chrysanthi, Kristof Van Hecke, Luc Van Meervelt, et al. “Novel Thermal and Microwave-assisted Facile Route to naphthalen-2(1H)-ones via an Oxidative Alkoxylation-ring-opening Protocol.” ORGANIC LETTERS 11.14 (2009): 2964–2967. Print.