Reinvestigating the Reaction of 1H-Pyrazol-5-amines with 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles
Publication type: Journal Article
Publication date: 2014-04-23
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
24734990
Organic Chemistry
Abstract
The reaction of Appel salt 1 with 1H-pyrazol-5-amines 2 gives main products N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1H-pyrazol-5-amines 3, and 6H-pyrazolo[3,4-c]isothiazole-3-carbonitriles 5, together with several minor side products. When the pyrazoles are N-1 methylated, the product ratio 3:5 can be modified by adjusting the pH of the reaction medium: acidic conditions favor formation of the dithiazolylidenes 3, while basic conditions favor formation of pyrazolo[3,4-c]isothiazoles 5. Furthermore, thermolysis of N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1H-pyrazol-5-amines 3 gives 1H-pyrazolo[3,4-d]thiazole-5-carbonitriles 4. Single crystal X-ray crystallography supports the structure of 4,6-dimethyl-6H-pyrazolo[3,4-c]isothiazole-3-carbonitrile (5a) and helps resolve a previous incorrect structural assignment of 1H-pyrazolo[3,4-d]thiazole-5-carbonitriles 4.
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Koyioni M. et al. Reinvestigating the Reaction of 1H-Pyrazol-5-amines with 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles // Journal of Organic Chemistry. 2014. Vol. 79. No. 9. pp. 4025-4037.
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Koyioni M., Manoli M., Manos M. J., Koutentis P. A. Reinvestigating the Reaction of 1H-Pyrazol-5-amines with 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles // Journal of Organic Chemistry. 2014. Vol. 79. No. 9. pp. 4025-4037.
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TY - JOUR
DO - 10.1021/jo500509e
UR - https://doi.org/10.1021/jo500509e
TI - Reinvestigating the Reaction of 1H-Pyrazol-5-amines with 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles
T2 - Journal of Organic Chemistry
AU - Koyioni, Maria
AU - Manoli, Maria
AU - Manos, Manolis J.
AU - Koutentis, Panayiotis A.
PY - 2014
DA - 2014/04/23
PB - American Chemical Society (ACS)
SP - 4025-4037
IS - 9
VL - 79
PMID - 24734990
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
Copy
@article{2014_Koyioni,
author = {Maria Koyioni and Maria Manoli and Manolis J. Manos and Panayiotis A. Koutentis},
title = {Reinvestigating the Reaction of 1H-Pyrazol-5-amines with 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles},
journal = {Journal of Organic Chemistry},
year = {2014},
volume = {79},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/jo500509e},
number = {9},
pages = {4025--4037},
doi = {10.1021/jo500509e}
}
Cite this
MLA
Copy
Koyioni, Maria, et al. “Reinvestigating the Reaction of 1H-Pyrazol-5-amines with 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles.” Journal of Organic Chemistry, vol. 79, no. 9, Apr. 2014, pp. 4025-4037. https://doi.org/10.1021/jo500509e.