Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide
Publication type: Journal Article
Publication date: 2011-09-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
The cyclocondensation of N-(prop-2-yn-1-yl)-o-phenylenediamines with phenyl isothiocyanate leads to the formation of 1-(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazole-2-thiones irrespective of the substituent nature at the triple bond. Reactions of both mono- and diacetylenic derivatives of o-phenylenediamine with carbon disulfide in the presence of KOH proceed with the formation of two heterocyclic nuclei simultaneously. From N-(prop-2-yn-1-yl)-o-phenylenediamines containing an aryl substituent at the triple bond, and N-(penta-2,4-diyn-1-yl)-o-phenylenediamines 2-methylidene-2,3-dihydro[1,3]thiazolo[3,2-a]benzimidazoles are formed. The latter are readily isomerized under the action of base giving thiazolo[3,2-a]benzimidazoles. The cyclocondensation of N-(alk-2-yn-1-yl)-o-phenylenediamines with CS2 leads to [1,3]thiazino[3,2-a]benzimidazoles.
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Novikov R. V., Danilkina N. A., Balova I. A. Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide // Chemistry of Heterocyclic Compounds. 2011. Vol. 47. No. 6. pp. 758-766.
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Novikov R. V., Danilkina N. A., Balova I. A. Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide // Chemistry of Heterocyclic Compounds. 2011. Vol. 47. No. 6. pp. 758-766.
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TY - JOUR
DO - 10.1007/s10593-011-0831-z
UR - https://doi.org/10.1007/s10593-011-0831-z
TI - Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide
T2 - Chemistry of Heterocyclic Compounds
AU - Novikov, R V
AU - Danilkina, N A
AU - Balova, I A
PY - 2011
DA - 2011/09/01
PB - Springer Nature
SP - 758-766
IS - 6
VL - 47
SN - 0009-3122
SN - 1573-8353
ER -
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BibTex (up to 50 authors)
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@article{2011_Novikov,
author = {R V Novikov and N A Danilkina and I A Balova},
title = {Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide},
journal = {Chemistry of Heterocyclic Compounds},
year = {2011},
volume = {47},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007/s10593-011-0831-z},
number = {6},
pages = {758--766},
doi = {10.1007/s10593-011-0831-z}
}
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Novikov, R. V., et al. “Cyclocondensation of n-(prop-2-yn-1-yl)- and n-(penta-2,4-diyn-1-yl)- o-phenylenediamines with phenyl isothiocyanate and carbon disulfide.” Chemistry of Heterocyclic Compounds, vol. 47, no. 6, Sep. 2011, pp. 758-766. https://doi.org/10.1007/s10593-011-0831-z.
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