Subscribe to RSS
DOI: 10.1055/a-2797-9503
Ruthenium-catalyzed C–H Sulfonamidation of 4-Aryl-7H-pyrrolo[2,3-d] pyrimidine with Sulfonyl Azides Under Aerobic Atmosphere
Authors
This work was supported by National Natural Science Foundation of China (No. 22277108, 21877099). Zhejiang Apeloa Pharmaceutical Co., Ltd. (No. KYY-HX-20200894), and Hangzhou Keysensing Co., Ltd. (No. KYY-HX-20241).
Supported by: National Natural Science Foundation of China 22277108, 21877099 Supported by: Zhejiang Apeloa Pharmaceutical Co., Ltd. KYY-HX-20200894

Abstract
Ruthenium-catalyzed arene ortho C−H sulfonamidation of 4-aryl-7H-pyrrolo[2,3-d]pyrimidine derivatives with sulfonyl azides under aerobic conditions is described. This transformation has the advantages of operational simplicity, good functional group compatibility, broad substrate scope, and mild conditions, affording a variety of sulfonamidated pyrrolo[2,3-d]pyrimidine derivatives in good to excellent yields. Oxygen plays a vital role in this unique reactivity.
Keywords
C–H sulfonamidation - Pyrrolo[2,3-d]pyrimidine - Sulfonyl azides - Site-selectivity - [RuCl2(p-cymene)]2 - Under aerobic conditionsPublication History
Received: 19 December 2025
Accepted after revision: 26 January 2026
Accepted Manuscript online:
27 January 2026
Article published online:
06 February 2026
© 2026. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Sk MR, Bera SS, Basuli S, Metya A, Maji MS. Asian J Org Chem 2020; 9: 1701-1717
- 2 Kumari S, Carmona AV, Tiwari AK, Trippier PC. J Med Chem 2020; 63: 12290-12358
- 3 Remko M. J Mol Struct 2010; 944: 34-42
- 4 Sosunovych B, Vashchenko BV, Andriashvili VA, Grygorenko OO. Chem Rec 2023; e202300258
- 5 Liu Z, Ebadi A, Toughani M, Mert N, Vessally E. RSC Adv 2020; 10: 37299-37313
- 6 Rao MVK, Kareem S, Vali SR, Reddy BVS. Org Biomol Chem 2023; 21: 8426-8462
- 7 Wishart DS, Feunang YD, Guo AC. et al. Nucleic Acids Res 2018; 46: D1074-D1082
- 8 Kim JY, Park SH, Ryu J, Cho SH, Kim SH, Chang S. J Am Chem Soc 2012; 134: 9110-9113
- 9 Shi J, Zhou B, Yang Y, Li Y. Org Biomol Chem 2012; 10: 8953-8955
- 10a Jia X, Han J. J Org Chem 2014; 79: 4180-4185
- 10b Wang H, Yu Y, Hong X, Tan Q, Xu B. J Org Chem 2014; 79: 3279-3288
- 10c Zhang C, Zhou Y, Deng Z, Chen X, Peng Y. Eur J Org Chem 2015; 1735-1744
- 10d Ma JL, Zhou XM, Chen JL. et al. Org Biomol Chem 2022; 20: 7554-7576
- 11a Yadav MR, Rit RK, Sahoo AK. Org Lett 2013; 15: 1638-1641
- 11b Bhanuchandra M, Yadav MR, Rit RK, Kurama MR, Sahoo AK. Chem Commun 2013; 49: 5225-5227
- 11c Kim J, Kim J, Chang S. Chem Eur J 2013; 19: 7328-7333
- 11d Thirunavukkarasu VS, Raghuvanshi K, Ackermann L. Org Lett 2013; 15: 3286-3289
- 11e Zhou X, Luo P, Long L, Ouyang M, Sang X, Ding Q. Tetrahedron 2014; 70: 6742-6748
- 11f Pan C, Abdukader A, Han J, Cheng Y, Zhu C. Chem Eur J 2014; 20: 3606-3609
- 11g Wang X, Zhang C, Li J. et al. RSC Adv 2016; 6: 68929-68933
- 11h Xiao X, Jia G, Liu F, Ou G, Xie Y. J Org Chem 2018; 83: 13811-13820
- 11i Bakthadoss M, Kumar PV, Kumar R, Surender M, Shadra DS. New J Chem 2019; 43: 14190-14195
- 12a Kong X, Lin L, Xu B. Adv Synth Catal 2018; 360: 2801-2805
- 12b Kong X, Xu B. Asian J Org Chem 2019; 8: 1862-1865
- 13 Hu Z, Luo S, Zhu Q. Sci China Chem 2015; 58: 1349-1353
- 14 Sun B, Yoshino T, Matsunaga S, Kanai M. Adv Synth Catal 2014; 356: 1491-1495
- 15a Lee D, Kim Y, Chang S. J Org Chem 2013; 78: 11102-11109
- 15b Shin K, Chang S. J Org Chem 2014; 79: 12197-12204
- 15c Hou W, Yang Y, Ai W. et al. Eur J Org Chem 2015; 395-400
- 15d Kim Y, Park J, Chang S. Org Lett 2016; 18: 1892-1895
- 15e Hermann GN, Becker P, Bolm C. Angew Chem Int Ed 2016; 55: 3781-3784
- 15f Chen S, Feng B, Zheng X, Yin J, Yang S, You J. Org Lett 2017; 19: 2502-2505
- 15g Lanke V, Prabhu KR. Chem Commun 2017; 53: 5117-5120
- 15h Wang L, Yang Z, Yang M, Zhang R, Kuai C, Cui X. Org Biomol Chem 2017; 15: 8302-8307
- 15i Hou H, Zhao Y, Sheng S. J Chen, Adv Synth Catal 2019; 361: 4393-4398
- 15j Xiong H, Gu Y, Zhang S. et al. Chem Commun 2020; 56: 4692-4695
- 16 Dinakaran VS, Bomma B, Srinivasan KK. Der Pharma Chem 2012; 4: 255-265
- 17a Zhou J, Mao ZT, Pan HK, Zhang XX. Org Chem Front 2020; 7: 324-328
- 17b Liu M, Mao ZT, Jiang YF, Zhang Z, Zhang XX. Tetrahedron Lett 2022; 96: 153754
- 17c Liu M, Shen CW, Tang T, Pan CH, Liu MR, Zhang XX. Org Lett 2023; 25: 2637-2641
- 18 Mao ZT, Liu M, Zhu GY, Zhou J, Zhang XX. Org Chem Front 2020; 7: 2696-2702
- 19 Jiang YF, Pan CH, Tang T, Liu MR, Zhang XX. Org Biomol Chem 2023; 21: 2748-2753
- 20 Pan CH, He C, Wang JR, Tang JY, Zhang XX. Org Biomol Chem 2024; 22: 1181-1185
- 21 Liu MR, Li N, Zhu QB. et al. Tetrahedron 2024; 155: 133912
- 22 Zhang Z, Liu MR, Liu M, Pan CH, Mao ZT, Zhang XX. J Org Chem 2024; 89: 2996-3009