New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole
Publication type: Journal Article
Publication date: 2011-12-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Treatment of 4-(1-adamantyl)-1,2,3-thiadiazole with potassium tert-butoxide generated potassium 2-(1-adamantyl)ethynethiolate which reacted with aromatic carboxylic acid chlorides to give unstable S-[2-(1-adamantyl)ethynyl] arenecarbothioates whose acid hydrolysis afforded S-[2-(1-adamantyl)-2-oxoethyl] arenecarbothioates. The latter reacted with ammonium acetate in acetic acid yielding 4-(1-adamantyl)-2-aryl-1,3-thiadiazoles. Reactions of 4-(1-adamantyl)-2-(4-chloro-3-nitrophenyl)-1,3-thiadiazole with cyclic secondary amines gave the corresponding products of nucleophilic replacement of the chlorine atom in the aromatic ring.
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Shchipalkin A. A., Petrov M., Kuznetsov V. A. New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole // Russian Journal of Organic Chemistry. 2011. Vol. 47. No. 12. pp. 1878-1881.
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Shchipalkin A. A., Petrov M., Kuznetsov V. A. New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole // Russian Journal of Organic Chemistry. 2011. Vol. 47. No. 12. pp. 1878-1881.
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TY - JOUR
DO - 10.1134/s1070428011120165
UR - https://doi.org/10.1134/s1070428011120165
TI - New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole
T2 - Russian Journal of Organic Chemistry
AU - Shchipalkin, A A
AU - Petrov, M.L.
AU - Kuznetsov, V. A.
PY - 2011
DA - 2011/12/01
PB - Pleiades Publishing
SP - 1878-1881
IS - 12
VL - 47
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2011_Shchipalkin,
author = {A A Shchipalkin and M.L. Petrov and V. A. Kuznetsov},
title = {New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole},
journal = {Russian Journal of Organic Chemistry},
year = {2011},
volume = {47},
publisher = {Pleiades Publishing},
month = {dec},
url = {https://doi.org/10.1134/s1070428011120165},
number = {12},
pages = {1878--1881},
doi = {10.1134/s1070428011120165}
}
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MLA
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Shchipalkin, A. A., et al. “New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole.” Russian Journal of Organic Chemistry, vol. 47, no. 12, Dec. 2011, pp. 1878-1881. https://doi.org/10.1134/s1070428011120165.