Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity
Publication type: Journal Article
Publication date: 2014-01-23
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Efficient routes for the regioselective synthesis of 3,5-bis(het)arylisoxazoles with complementary regioselectivity have been developed. The methods involve the cyclocondensation of hydroxylamine hydrochloride with either 1,3-bis(het)aryl-monothio-substituted 1,3-diketones 1 or with 3-methylthio-1,3-bis(het)aryl-2-propenones 2 under various reaction conditions. In the first protocol, diketones 1 were treated with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene to give 3,5-bis(het)arylisoxazoles 5, in which the het(aryl) moiety attached to thiocarbonyl group of the monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het)arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors 1 and 2 has been suggested.
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Raghava B. et al. Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity // European Journal of Organic Chemistry. 2014. Vol. 2014. No. 9. pp. 1882-1892.
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Raghava B., Parameshwarappa G., Acharya A., Swaroop T. R., Rangappa K., Ila H. Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity // European Journal of Organic Chemistry. 2014. Vol. 2014. No. 9. pp. 1882-1892.
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TY - JOUR
DO - 10.1002/ejoc.201301667
UR - https://doi.org/10.1002/ejoc.201301667
TI - Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity
T2 - European Journal of Organic Chemistry
AU - Raghava, Byregowda
AU - Parameshwarappa, Gangajji
AU - Acharya, Anand
AU - Swaroop, Toreshettahally R
AU - Rangappa, K.
AU - Ila, H
PY - 2014
DA - 2014/01/23
PB - Wiley
SP - 1882-1892
IS - 9
VL - 2014
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2014_Raghava,
author = {Byregowda Raghava and Gangajji Parameshwarappa and Anand Acharya and Toreshettahally R Swaroop and K. Rangappa and H Ila},
title = {Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity},
journal = {European Journal of Organic Chemistry},
year = {2014},
volume = {2014},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/ejoc.201301667},
number = {9},
pages = {1882--1892},
doi = {10.1002/ejoc.201301667}
}
Cite this
MLA
Copy
Raghava, Byregowda, et al. “Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity.” European Journal of Organic Chemistry, vol. 2014, no. 9, Jan. 2014, pp. 1882-1892. https://doi.org/10.1002/ejoc.201301667.