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A novel efficient protocol for preparation of 3-formyl-2-arylbenzo[b]furan derivatives.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . May2014, Vol. 55 Issue 21, p3274-3277. 4p. - Publication Year :
- 2014
-
Abstract
- Abstract: An efficient method for preparation of 3-formyl-2-arylbenzo[b]furan derivatives 4 from 3-chloro-2-(2-methoxyaryl)-1-arylprop-2-en-1-one 2 was developed, and the desired product was obtained in good to excellent yields. By converting 2-(2-methoxyphenyl)-3-oxo-3-phenylpropanal 1 to 2, the regioselectivity problem occurring in the reaction when using 1 as the starting material was successfully avoided. Furthermore, a one-pot procedure for the successive demethylation, cyclization, and hydrolysis was evolved, although the intermediate 3-(dibromomethyl)-2-phenylbenzo[b]furan 3a could be isolated. A plausible mechanism was proposed based on some in situ investigations. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 55
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 96020732
- Full Text :
- https://doi.org/10.1016/j.tetlet.2014.04.050