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-00000084.xml
Download PDF
Synthesis 2022; 54(09): 2185-2192
DOI: 10.1055/s-0040-1719880
DOI: 10.1055/s-0040-1719880
paper
Oxidant-Free Selective Synthesis of Functionalized Chroman-4-ones from ortho-Hydroxyacetophenones under HOAc/DMSO Conditions
Financial support from the National Natural Science Foundation of China (21702002) and the National College Students Innovation and Entrepreneurship Training Program (202110364407) is gratefully acknowledged.
Abstract
A metal-free and oxidant-free acid-promoted DMSO activation and subsequent reaction is reported. In this protocol, two molecules of DMSO are activated by HOAc and serve as dual synthons which react with ortho-hydroxyacetophenones, affording 3-(methylthiomethyl)chroman-4-ones in moderate to good yields with high selectivity.
Key words
ortho-hydroxyacetophenones - chroman-4-ones - dimethyl sulfoxide - dual synthons - benzopyranopyrimidinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719880.
- Supporting Information
Publication History
Received: 27 October 2021
Accepted after revision: 13 December 2021
Article published online:
26 January 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Reis J, Gaspar A, Milhazes N, Borges F. J. Med. Chem. 2017; 60: 7941
- 1b Santos CM. M, Silva AM. S. Eur. J. Org. Chem. 2017; 31
- 1c Emami S, Ghanbarimasir Z. Eur. J. Med. Chem. 2015; 93: 539
- 1d Seifert T, Malo M, Kokkola T, Engen K, Fridén-Saxin M, Wallén EA. A, Lahtela-Kakkonen M, Jarho EM, Luthman K. J. Med. Chem. 2014; 57: 9870
- 1e Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chem. Rev. 2014; 114: 4960
- 2a Mitra RN, Show K, Barman D, Sarkar S, Maiti DK. J. Org. Chem. 2019; 84: 42
- 2b Zhao M, Liu J.-L, Liu H.-F, Chen J, Zhou L. Org. Lett. 2018; 20: 2676
- 2c Piel I, Steinmetz M, Hirano K, Fröhlich R, Grimme S, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 4983
- 2d Biju AT, Wurz NE, Glorius F. J. Am. Chem. Soc. 2010; 132: 5970
- 3a Sheng J, Liu J, Chen L, Zhang L, Zheng L, Wei X. Org. Chem. Front. 2019; 6: 1471
- 3b Hu H, Chen X, Sun K, Wang J, Liu Y, Liu H, Yu B, Sun Y, Qu L, Zhao Y. Org. Chem. Front. 2018; 5: 2925
- 3c Liu Z, Bai Y, Zhang J, Yu Y, Tan Z, Zhu G. Chem. Commun. 2017; 53: 6440
- 4a Huang H.-L, Du J.-Y, Li Q.-L, Gao F, Ma C.-L. J. Org. Chem. 2020; 85: 3963
- 4b Zhou N, Wu M, Zhang M, Zhou X. Asian J. Org. Chem. 2019; 8: 828
- 4c Zhou Y, Xiong Z, Qiu J, Kong L, Zhu G. Org. Chem. Front. 2019; 6: 1022
- 4d He X.-K, Cai B.-G, Yang Q.-Q, Wang L, Xuan J. Chem. Asian J. 2019; 14: 3269
- 4e Jung S, Kim J, Hong S. Adv. Synth. Catal. 2017; 359: 3945
- 4f Lu D, Wan Y, Kong L, Zhu GV. Org. Lett. 2017; 19: 2929
- 5 Tang L, Yang Z, Chang X, Jiao J, Ma X, Rao W, Zhou Q, Zheng L. Org. Lett. 2018; 20: 6520
- 6a Hu H, Chen X, Sun K, Wang J, Liu Y, Liu H, Fan L, Yu B, Sun Y, Qu L, Zhao Y. Org. Lett. 2018; 20: 6157
- 6b Yang W.-C, Dai P, Luo K, Ji Y.-G, Wu L. Adv. Synth. Catal. 2017; 359: 2390
- 7 Zhao J, Li P, Li X, Xia C, Li F. Chem. Commun. 2016; 52: 3661
- 8a Liu Y, Hu Y, Cao Z, Zhan X, Luo W, Liu Q, Guo C. Adv. Synth. Catal. 2019; 361: 1084
- 8b Liu Y, Zhan X, Ji P, Xu J, Liu Q, Luo W, Chen T, Guo C. Chem. Commun. 2017; 53: 5346
- 9a Tashrifi Z, Khanaposhtani MM, Larijani B, Mahdavi M. Adv. Synth. Catal. 2020; 362: 65
- 9b Xiang J.-C, Gao Q.-H, Wu A.-X. The Applications of DMSO. In Solvents as Reagents in Organic Synthesis: Reactions and Applications. Wu X.-F. Wiley-VCH; Weinheim: 2017: 315-353
- 9c Jones-Mensah E, Karki M, Magolan J. Synthesis 2016; 48: 1421
- 9d Wu X.-F, Natte K. Adv. Synth. Catal. 2016; 358: 336
- 10a Chang M.-Y, Chen K.-T. Synthesis 2021; 53: 135
- 10b Fan J, Zhao Y, Zhang J, Xie M, Zhang Y. J. Org. Chem. 2020; 85: 691
- 10c Kumari S, Shakoor SM. A, Markad D, Mandal SK, Sakhuja R. Eur. J. Org. Chem. 2019; 705
- 10d Ebule R, Mudshinge S, Nantz MH, Mashuta MS, Hammond GB, Xu B. J. Org. Chem. 2019; 84: 324
- 10e Chang MY, Chen HY, Tsai YL. Org. Lett. 2019; 21: 1832
- 10f Zheng K, Zhuang S, Shu W, Wu Y, Yang C, Wu A. Chem. Commun. 2018; 54: 11897
- 10g Xie C, Zhang Z, Li D, Gong J, Han X, Liu X, Ma C. J. Org. Chem. 2017; 82: 3491
- 10h Wen Z.-K, Liu X.-H, Liu Y.-F, Chao J.-B. Org. Lett. 2017; 19: 5798
- 11a Fu D, Dong J, Wang J, Xu J. Asian J. Org. Chem. 2021; 10: 1756
- 11b Fu D, Wang J, Xu J. Synthesis 2021; 53: 4086
- 11c Zhang Y, Kuang J, Xiao X, Wang L, Ma Y. Org. Lett. 2021; 23: 3960
- 11d Li H, Su M, Nie Z, Yang T, Luo W, Liu Q, Guo C. Adv. Synth. Catal. 2021; 363: 3127
- 11e Xu C, Jiang S.-F, Wen X.-H, Zhang Q, Zhou Z.-W, Wu Y, Jia F.-C, Wu A. Adv. Synth. Catal. 2018; 360: 2267
- 12a Wang A, Liu X, Kong Y, Wang J, Jiang T.-S. Org. Chem. Front. 2021; 8: 947
- 12b Jiang T.-S, Zhou Y, Dai L, Liu X, Zhang X. Tetrahedron Lett. 2019; 60: 2078
- 12c Jiang T.-S, Wang X, Zhang X. Tetrahedron Lett. 2018; 59: 2979
- 13 Akram MO, Bera S, Patil NT. Chem. Commun. 2016; 52: 12306
- 14 Dubrovskiy AV, Larock RC. Org. Lett. 2010; 12: 3117
- 15 Gogoi J, Gogoi P, Bezbaruah P, Boruah RC. Tetrahedron Lett. 2013; 54: 7136
Selected reviews on the synthesis and biological activities of chroman-4-ones:
For recent examples see the following, and references cited therein:
Recent examples of transition-metal-catalyzed synthesis:
Recent examples of photoredox synthesis:
Recent reviews on DMSO-involved reactions:
Selected examples of protic acid promoted DMSO transformations:
Recent examples of DMSO serving as a dual synthon: