Synthesis of 3-Substituted Chromones through Photoactivation of Acceptor–Acceptor Diazo Compounds

Prashant Kumar; Asit Kumar; Ruchir Kant; Sanjeev K. Shukla; Namrata Rastogi

doi:10.1055/s-0040-1720134

Synthesis, Table of Contents

Synthesis 2024; 56(24): 3785-3792
DOI: 10.1055/s-0040-1720134

paper

Recent Advancements in the Chemistry of Diazo Compounds

Synthesis of 3-Substituted Chromones through Photoactivation of Acceptor–Acceptor Diazo Compounds

Prashant Kumar

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

,

Asit Kumar

^cSophisticated Analytical Instrument Facility & Research Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India

,

Ruchir Kant

^dBiochemistry & Structural Biology Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India

,

Sanjeev K. Shukla

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

^cSophisticated Analytical Instrument Facility & Research Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India

,

Namrata Rastogi ∗

^aMedicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

› Author Affiliations

Abstract

All articles of this category

Abstract

We report the photocatalytic alkylation of o-hydroxyarylenaminones with acceptor–acceptor diazo compounds to access 3-alkyl chromones. The reaction involves triplet sensitization of the diazo substrate via energy transfer from the photosensitizer. The notable features of the protocol are operational simplicity, wide substrate scope, and generally high yields of the products.

Key words

o-hydroxyarylenaminone - A–A diazo compounds - energy transfer - triplet carbine - alkyl chromone

Full Text

References

References

For selected reviews on diazo compounds, see:

1a Ford A, Miel H, Ring A, Slattery CN, Maguire AR, McKervey MA. Chem. Rev. 2015; 115: 9981
1b Xiang Y, Wang C, Ding Q, Peng Y. Adv. Synth. Catal. 2019; 361: 919
1c Mykhailiuk PK. Chem. Rev. 2020; 120: 12718
1d Lübcke M, Szabó KJ. Synlett 2021; 32: 1060
1e Dong S, Liu X, Feng X. Acc. Chem. Res. 2022; 55: 415
1f Wang J. Tetrahedron Lett. 2022; 108: 154135
1g Timmann S, Alcarazo M. Chem. Commun. 2023; 59: 8032

For selected reviews on transition-metal-mediated diazo insertions, see:

2a Wang B, Qui D, Zhang Y, Wang J. Beilstein J. Org. Chem. 2016; 12: 796
2b Fructos MR, Dίaz-Requejo MM, Pérez PJ. Chem. Commun. 2016; 52: 7326
2c Dasgupta A, Richards E, Melen RL. ACS Catal. 2022; 12: 442
2d He Y, Huang Z, Wu K, Ma J, Zhou Y.-G, Yu Z. Chem. Soc. Rev. 2022; 51: 2759
2e Pramanik M, Melen RL. Synthesis 2023; 55: 3906
2f Bera S, Jana S, Samanta R. Synthesis 2024; 56: 29

For selected reviews on visible-light-mediated chemistry of diazo compounds, see:

3a Yang Z, Stivanin ML, Jurberg ID, Koenigs RM. Chem. Soc. Rev. 2020; 49: 6833
3b Durka J, Turkowska J, Gryko D. ACS Sustainable Chem. Eng. 2021; 9: 8895
3c Empel C, Pei C, Koenigs RM. Chem. Commun. 2022; 58: 2788
3d Gallo RD. C, Cariello G, Goulart TA. C, Jurberg ID. Chem. Commun. 2023; 59: 7346
3e Zhang Z, Gevorgyan V. Chem. Rev. 2024; 124: 7214

4 Jurberg ID, Davies HM. L. Chem. Sci. 2018; 9: 5112

For representative examples of visible-light-mediated diazo insertions, see:

5a Empel C, Patureau FW, Koenigs RM. J. Org. Chem. 2019; 84: 11316
5b Hommelsheim R, Guo Y, Yang Z, Empel C, Koenigs RM. Angew. Chem. Int. Ed. 2019; 58: 1203
5c He F, Koenigs RM. Chem. Commun. 2019; 55: 4881
5d Stivanin ML, Fernandes AA. G, da Silva AF, Okada CY. Jr, Jurberg ID. Adv. Synth. Catal. 2020; 362: 1106
5e Yang J, Wang G, Chen S, Ma B, Zhou H, Song M, Liu C, Huo CC. Org. Biomol. Chem. 2020; 18: 9494
5f Maiti D, Das R, Sen S. J. Org. Chem. 2021; 86: 2522
5g Guo W, Zhou Y, Xie H, Yue X, Jiang F, Huang H, Han Z, Sun J. Chem. Sci. 2023; 14: 843
5h Xia S, Jian Y, Zhang L, Zhang C, An Y, Wang Y. RSC Adv. 2023; 13: 14501

6a He Y, Chen H, Li L, Huang J, Xiao T, Anand D, Zhou L. J. Photochem. Photobiol., A 2018; 355: 220
6b Nagode SB, Kant R, Rastogi N. Org. Lett. 2019; 21: 6249
6c Devi L, Pokhriyal A, Shekhar S, Kant R, Mukherjee S, Rastogi N. Asian J. Org. Chem. 2021; 10: 3328
6d Karmakar U, Hwang HS, Lee Y, Cho EJ. Org. Lett. 2022; 24: 6137

7a Xia X.-D, Ren Y.-L, Chen J.-R, Yu X.-L, Lu L.-Q, Zou Y.-Q, Wan J, Xiao W.-J. Chem. Asian J. 2015; 10: 124
7b Strieth-Kalthoff F, James MJ, Teders M, Pitzer L, Glorius F. Chem. Soc. Rev. 2018; 47: 7190
7c Zhu S, Li F, Empel C, Jana S, Pei C, Koenigs RM. Adv. Synth. Catal. 2022; 364: 3149

8 Bagle PN, Mane MV, Sancheti SP, Gade AB, Shaikh SR, Baik M.-H, Patil NT. Org. Lett. 2019; 21: 335
9 Zhao W, He Z, Yang X, Yu Y, Baell JB, Huang F. J. Org. Chem. 2023; 88: 13634

10a Sharma KS, Kumar S, Chand K, Kathuria A, Gupta A, Jain R. Curr. Med. Chem. 2011; 18: 3825
10b Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chem. Rev. 2014; 114: 4960
10c Silva CF. M, Pinto CG. A, Silva AM. S. ChemMedChem 2016; 11: 2252
10d Madhav H, Jameel E, Rehan M, Hoda N. RSC Med. Chem. 2022; 13: 258

11a Rotzoll S, Appel B, Langer P. Tetrahedron Lett. 2005; 46: 4057
11b Zhang M, Gong Y, Zhou W, Zhou Y, Liu X.-L. Org. Chem. Front. 2021; 8: 3968
11c Langer P. Synlett 2022; 33: 207
11d Langer P. Beilstein J. Org. Chem. 2024; 20: 1256
11e Liu X.-L, Gong Y, Chen S, Zuo X, Yao Z, Zhou Y. Org. Chem. Front. 2019; 6: 1603

12a Chang S.-Q, Zou X, Gong Y, He X.-W, Liu X.-L, Zhou Y. Chem. Commun. 2019; 55: 14003
12b Liu X.-L, Zhou G, Gong Y, Yao Z, Zuo X, Zhang W.-H, Zhou Y. Org. Lett. 2019; 21: 2528
12c Fu L, Xu Z, Wan J.-P, Liu Y. Org. Lett. 2020; 22: 9518
12d Fang Y.-C, Chen J.-H, Xiu R.-F, Zhang L.-R, Zheng F.-H, Chen Y.-Z, Gao Z.-W, Han W.-Y. Org. Chem. Front. 2023; 10: 3752
12e Tong Q, Xiu R.-F, Chen J.-H, Zhang Y, Cui B.-D, Wan N.-W, Chen Y.-Z, Han W.-Y. ACS Catal. 2023; 13: 12692
12f Sharma MK, Tiwari B, Hussain N. Chem. Commun. 2024; 60: 14003

13 CCDC 2367617 (3b) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
14 Koike T, Akita M. Inorg. Chem. Front. 2014; 1: 562
15 For triplet energies of photosensitizers, see: Lee W, Koo Y, Jung H, Chang S, Hong S. Nat. Chem. 2023; 15: 1091

16a Jha N, Singh RP, Saxena P, Kapur M. Org. Lett. 2021; 23: 8694
16b Liu C, Feng T, Wu X, Zhu C. ACS Catal. 2023; 13: 8394

Supplementary Material

Supporting Information