Na2S2O5 Mediated Synthesis of Bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes from Pyrazolo[1,5-a]pyrimidines Using DMSO as C1 Synthon
Publication type: Journal Article
Publication date: 2024-09-25
scimago Q3
wos Q3
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Abstract
We report an unprecedented synthesis of bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes, a new class of di(hetaryl)methanes, from pyrazolo[1,5-a]pyrimidines by using DMSO as a C1 synthon (methylene source). The transformation is mediated by sodium metabisulfite (Na2S2O5), which plays a crucial role in the presence of acetic acid as a promoter. A wide variety of bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes were synthesized in moderate to good yields of up to 90%. Mechanistic studies suggested that the reaction follows an ionic pathway, probably involving a methyl(methylene)sulfonium ion as an active electrophilic species formed in situ by the reaction of DMSO with Na2S2O5.
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4
Total citations:
4
Citations from 2024:
3
(75%)
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Pattanayak P. et al. Na2S2O5 Mediated Synthesis of Bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes from Pyrazolo[1,5-a]pyrimidines Using DMSO as C1 Synthon // Synlett. 2024. Vol. 35. No. 20. pp. 2465-2470.
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Saha S., Keerthana H. S., Naresh A., Pattanayak P., Satyanarayana A. N. V., Girase Y. K. Na2S2O5 Mediated Synthesis of Bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes from Pyrazolo[1,5-a]pyrimidines Using DMSO as C1 Synthon // Synlett. 2024. Vol. 35. No. 20. pp. 2465-2470.
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TY - JOUR
DO - 10.1055/a-2422-1416
UR - http://www.thieme-connect.de/DOI/DOI?10.1055/a-2422-1416
TI - Na2S2O5 Mediated Synthesis of Bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes from Pyrazolo[1,5-a]pyrimidines Using DMSO as C1 Synthon
T2 - Synlett
AU - Saha, Samiran
AU - Keerthana, Hariharasubramanian Sai
AU - Naresh, Ainala
AU - Pattanayak, Paramita
AU - Satyanarayana, Appanapalli N V
AU - Girase, Yogesh K.
PY - 2024
DA - 2024/09/25
PB - Georg Thieme Verlag KG
SP - 2465-2470
IS - 20
VL - 35
SN - 0936-5214
SN - 1437-2096
ER -
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@article{2024_Pattanayak,
author = {Samiran Saha and Hariharasubramanian Sai Keerthana and Ainala Naresh and Paramita Pattanayak and Appanapalli N V Satyanarayana and Yogesh K. Girase},
title = {Na2S2O5 Mediated Synthesis of Bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes from Pyrazolo[1,5-a]pyrimidines Using DMSO as C1 Synthon},
journal = {Synlett},
year = {2024},
volume = {35},
publisher = {Georg Thieme Verlag KG},
month = {sep},
url = {http://www.thieme-connect.de/DOI/DOI?10.1055/a-2422-1416},
number = {20},
pages = {2465--2470},
doi = {10.1055/a-2422-1416}
}
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MLA
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Pattanayak, Paramita, et al. “Na2S2O5 Mediated Synthesis of Bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes from Pyrazolo[1,5-a]pyrimidines Using DMSO as C1 Synthon.” Synlett, vol. 35, no. 20, Sep. 2024, pp. 2465-2470. http://www.thieme-connect.de/DOI/DOI?10.1055/a-2422-1416.