Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett
DOI: 10.1055/a-2526-0771
DOI: 10.1055/a-2526-0771
account
Recent Advances in the Synthesis of Functionalized Pyrazolo[1,5-a]pyrimidines via C–H Functionalization
A.K.B. acknowledges the Department of Science and Technology and Biotechnology (DSTBT), Government of West Bengal, India (GO no. 324(Sanc.)/STBT-11012(25)/13/2024-ST SEC) for financial support. A.K.B. also acknowledges the financial support from the SERB, DST (File no. EEQ/2018/000498) and the University of Kalyani (PRG). S. P. (CSIR-SRF), T. C. (URS-SRF) and S. D. (UGC-SRF) acknowledge the Council of Scientific and Industrial Research (CSIR) New Delhi, University of Kalyani, and University Grants Commission (UGC), New Delhi, respectively, for their fellowships.
This article is dedicated to Prof. B. C. Ranu on the grand occasion of his 75th birthday
Abstract
Recent developments in the synthesis of functionalized pyrazolo[1,5-a]pyrimidines through C–H functionalization have been summarized in this account, covering the synthesis of 3-halo, 3-nitro, 3-formyl, 3-acetyl, 3-sulfenyl, 3-selenyl, and 3-thiocyanato pyrazolo[1,5-a]pyrimidines and bis(pyrazolo[1,5-a]pyrimidin-3-yl)methanes. The main focus highlights the utilization of sustainable conditions in designing the protocols. Mechanistic aspects of these protocols have also been discussed in detail.
1 Introduction
2 Discussion
2.1 Synthesis of 3-Halo Pyrazolo[1,5-a]pyrimidines
2.2 Synthesis of 3-Nitro Pyrazolo[1,5-a]pyrimidines
2.3 Synthesis of 3-Formyl Pyrazolo[1,5-a]pyrimidine
2.4 Synthesis of 3-Acetyl Pyrazolo[1,5-a]pyrimidines
2.5 Synthesis of 3-Sulfenyl Pyrazolo[1,5-a]pyrimidines
2.6 Synthesis of 3-Selenyl Pyrazolo[1,5-a]pyrimidines
2.7 Synthesis of 3-Thiocyanated Pyrazolo[1,5-a]pyrimidines
2.8 Synthesis of Bis(pyrazolo[1,5-a]pyrimidinyl)methanes
3 Conclusions and Outcome
Key words
pyrazolo[1,5-a]pyrimidines - C–H functionalization - photocatalysis - electrocatalysis - green chemistryPublication History
Received: 09 January 2025
Accepted: 27 January 2025
Accepted Manuscript online:
27 January 2025
Article published online:
24 April 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Zisapel N. Expert Opin. Invest. Drugs 2015; 24: 401
-
2a
Arnold SL,
Zhengming C,
Phil S.
US2008045547A1, 2008
-
2b
Koilpillai JP,
Kale SA,
Kelkar LM,
Zope SS,
Khan MA.
US2012028045A1, 2012
- 3a Mackman RL, Sangi M, Sperandio D, Parrish JP, Eisenberg E, Perron M, Hui H, Zhang L, Siegel D, Yang H, Saunders O, Boojamra C, Lee G, Samuel D, Babaoglu K, Carey A, Gilbert BE, Piedra PA, Strickley R, Iwata Q, Hayes J, Stray K, Kinkade A, Theodore D, Jordan R, Desai M, Cihlar T. J. Med. Chem. 2015; 58: 1630
- 3b Nishio S, Abe M, Ito H. Diabetes, Metab. Syndr. Obes.: Targets Ther. 2015; 18: 163
- 4 Gupta A, Das R, Chamoli A, Choithramani A, Kumar H, Patel S, Khude D, Bothra G, Wangdale K, Chowdhury MG, Rathod R, Mandoli A, Shard A. Organometallics 2022; 41: 2365
- 5 Ledieu MS, Helyer NL. Ann. Appl. Biol. 1983; 102: 275
- 6a Tigreros A, Aranzazu S.-L, Bravo N.-F, Zapata-Rivera J, Portilla J. RSC Adv. 2020; 10: 39542
- 6b Singsardar M, Sarkar R, Majhi K, Sinha S, Hajra A. ChemistrySelect 2018; 3: 1404
- 7 Tigreros A, Zapata-Rivera J, Portilla J. ACS Sustainable Chem. Eng. 2021; 9: 12058
- 8 Tigreros A, Macías M, Portilla J. Dyes Pigm. 2022; 202: 110299
- 9 Tigreros A, Macías M, Portilla J. ChemPhotoChem 2022; 6: e202200133
- 10 Eicher T, Hauptmann S, Speicher A. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications . Wiley-VCH; Weinheim: 2003
- 11a Dhawa U, Kaplaneris N, Ackermann L. Org. Chem. Front. 2021; 8: 4886
- 11b Aricò F. Front. Chem. 2020; 8: 74
- 11c Constable DJ. C, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL. Jr, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY. Green Chem. 2007; 9: 411
- 12a Guillemard L, Kaplaneris N, Ackermann L, Johansson MJ. Nat. Rev. Chem. 2021; 5: 522
- 12b Pal T, Lahiri GK, Maiti D. Eur. J. Org. Chem. 2020; 2020: 6859
- 12c Davies HM. L, Morton D. J. Org. Chem. 2016; 81: 343
- 13a Yoshimura A, Zhdankin VV. Chem. Rev. 2024; 124: 11108
- 13b Bhanja R, Bera SK, Mal P. Adv. Synth. Catal. 2024; 366: 168
- 13c Mondal M, Ghosh S, Lai D, Hajra A. ChemSusChem 2024; 17: e202401114
- 13d Roy S, Panja S, Sahoo SR, Chatterjee S, Maiti D. Chem. Soc. Rev. 2023; 52: 2391
- 13e Baroliya PK, Dhaker M, Panja S, Al-Thabaiti SA, Albukhari SM, Alsulami QA, Dutta A, Maiti D. ChemSusChem 2023; 16: e202202201
- 13f Laskar R, Pal T, Bhattacharya T, Maiti S, Akita M, Maiti D. Green Chem. 2022; 24: 2296
- 13g Sinha SK, Guin S, Maiti S, Biswas JP, Porey S, Maiti D. Chem. Rev. 2022; 122: 5682
- 13h Bagdi AK, Rahman M, Bhattacherjee D, Zyryanov GV, Ghosh S, Chupakhin ON, Hajra A. Green Chem. 2020; 22: 6632
- 13i Parvatkar PT, Manetsch R, Banik BK. Chem. Asian J. 2019; 14: 6
- 14a Frecentese F, Sodano F, Corvino A, Schiano ME, Magli E, Albrizio S, Sparaco R, Andreozzi G, Nieddu M, Rimoli MG. Int. J. Mol. Sci. 2023; 24: 10722
- 14b Dhanush PC, Saranya PV, Anilkumar G. Tetrahedron 2022; 105: 132614
- 14c Yang H, Huang N, Wang N, Shen H, Teng F, Liu X, Jiang H, Tan M.-C, Gui Q.-W. ACS Omega 2021; 6: 25940
- 14d Besson T, Fruit C. Synthesis 2016; 48: 3879
- 15a Kumar H, Das R, Choithramani A, Gupta A, Khude D, Bothra G, Shard A. ChemistrySelect 2021; 6: 5807
- 15b Arias-Gómez A, Godoy A, Portilla J. Molecules 2021; 26: 2708
- 15c Salem MA, Helal MH, Gouda MA, Abd EL-Gawad HH, Shehab MA. M, El-Khalafawy A. Synth. Commun. 2019; 49: 1750
- 15d Cherukupalli S, Karpoormath R, Chandrasekaran B, Hampannavar GA, Thapliyal N, Palakollu VN. Eur. J. Med. Chem. 2017; 126: 298
- 16a Jismy B, Tikad A, Akssira M, Guillaumet G, Abarbri M. Molecules 2020; 25: 2062
- 16b Kirkpatrick WE, Okabe T, Hillyard IW, Robins RK, Dren AT, Novinson T. J. Med. Chem. 1977; 20: 386
- 17 Castillo J.-C, Rosero H.-A, Portilla J. RSC Adv. 2017; 7: 28483
- 18 Sikdar P, Choudhuri T, Paul S, Das S, Bagdi AK. ACS Omega 2023; 8: 23851
- 19 Chillal AS, Bhawale RT, Kshirsagar UA. RSC Adv. 2024; 14: 13095
- 20 Paul S, Das S, Choudhuri T, Sikdar P, Bagdi AK. Chem. Asian J. 2025; 20: e202401101
- 21a Castillo J.-C, Tigreros A, Portilla J. J. Org. Chem. 2018; 83: 10887
- 21b Correction: Castillo J.-C, Tigreros A, Cifuentes C, Portilla J. J. Org. Chem. 2024; 89: 14606
- 22 Aranzazu S.-L, Tigreros A, Arias-Gómez A, Zapata-Rivera J, Portilla J. J. Org. Chem. 2022; 87: 9839
- 23 Paul S, Das S, Choudhuri T, Sikdar P, Bagdi AK. J. Org. Chem. 2023; 88: 4187
- 24 Chillal AS, Bhawale RT, Sharma S, Kshirsagar UA. J. Org. Chem. 2024; 89: 14496
- 25 Choudhuri T, Paul S, Das S, Pathak DD, Bagdi AK. J. Org. Chem. 2023; 88: 8992
- 26 Sikdar P, Choudhuri T, Paul S, Das S, Kumar A, Bagdi AK. Synthesis 2023; 55: 3693
- 27 Chillal AS, Bhawale RT, Kshirsagar UA. ChemistrySelect 2024; 9: e202304815
- 28 Choudhuri T, Paul S, Sikdar P, Das S, Sawant SD, Bagdi AK. New J. Chem. 2024; 48: 9480
- 29 Kokorekin VA, Yaubasarova RR, Neverov SV, Petrosyan VA. Eur. J. Org. Chem. 2019; 2019: 4233
- 30 Pattanayak P, Satyanarayana AN. V, Chatterjee T. J. Org. Chem. 2024; 89: 13215
- 31 Zhang X, Chen J, Chen R, Wang L, Ma Y. Adv. Synth. Catal. 2024; 366: 3591
- 32 Pattanayak P, Satyanarayana AN. V, Saha S, Keerthana HS, Naresh A, Girase YK, Chatterjee T. Synlett 2024; 35: 2465