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
Synthesis
DOI: 10.1055/a-2367-1877
DOI: 10.1055/a-2367-1877
paper
β-Nitroacrylates and Phenols as Key Precursors of Arenofuran-3-carboxylates
We gratefully acknowledge financial support from the Università degli Studi di Camerino (University of Camerino). The research network Consorzio Interuniversitario Nazionale di ricerca in Metodologie e Processi Innovativi di Sintesi - Bari (CINMPIS-Bari) is also gratefully acknowledged.
Abstract
Herein we report a new, practical and efficient preparation of benzofuran-3-carboxylates and naphthofuran-3-carboxylates starting from β-nitroacrylates and phenols. The reaction is promoted by indium trichloride and leads to the target compounds in good to very good yields under microwave irradiation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2367-1877.
- Supporting Information
Publication History
Received: 07 May 2024
Accepted after revision: 16 July 2024
Accepted Manuscript online:
16 July 2024
Article published online:
05 August 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Ballini R, Gabrielli S, Palmieri A. Curr. Org. Chem. 2010; 14: 65
- 1b Gabrielli S, Chiurchiù E, Palmieri A. Adv. Synth. Catal. 2019; 36: 630
- 2a Palmieri A, Gabrielli S, Lanari D, Vaccaro L, Ballini R. Adv. Synth. Catal. 2011; 353: 1425
- 2b Chiurchiù E, Patehebieke Y, Gabrielli S, Ballini R, Palmieri A. Adv. Synth. Catal. 2019; 361: 2042
- 2c Palmieri A. Eur. J. Org. Chem. 2020; 4247
- 2d Zeng H.-W, Wu P.-Y, Wu H.-L. Org. Biomol. Chem. 2020; 18: 2991
- 3a Hiremathad A, Patil MR, Chetana KR, Chand K, Santos MA, Keri RS. RSC Adv. 2015; 5: 96809
- 3b Shamsuzzaman HK. Eur. J. Med. Chem. 2015; 97: 483
- 3c Miao Y.-H, Hu Y.-H, Yang J, Liu T, Sun J, Wang X.-J. RSC Adv. 2019; 9: 27510
- 3d Arce-Ramos L, Castillo J.-C, Becerra D. Pharmaceuticals 2023; 16: 1265
- 4a Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
- 4b Welsch ME, Snyder SA, Stockwell BR. Curr. Opin. Chem. Biol. 2010; 14: 347
- 4c Patel P, Shakya R, Vishakha, Asati V, Kurmi BD, Verma SK, Gupta GD, Rajak H. J. Mol. Struct. 2024; 1299: 137098
- 5a Pieters L, Van Dyck S, Gao M, Bai R, Hamel E, Vlietinck A, Lemière G. J. Med. Chem. 1999; 42: 5475
- 5b Chen Y, Chen S, Lu X, Cheng H, Ou Y, Cheng H, Zhou G.-C. Bioorg. Med. Chem. Lett. 2009; 19: 1851
- 5c Ryu C.-K, Song AL, Lee JY, Hong JA, Yoon JH, Kim A. Bioorg. Med. Chem. Lett. 2010; 20: 6777
- 5d Thévenin M, Thoret S, Grellier P, Dubois J. Bioorg. Med. Chem. 2013; 21: 4885
- 5e Yadav P, Singh P, Tewari AK. Bioorg. Med. Chem. Lett. 2014; 24: 2251
- 6a Liu Y, Wang H, Wan J.-P. J. Org. Chem. 2014; 79: 10599
- 6b Wan J.-P, Wang H, Liu Y, Ding H. Org. Lett. 2014; 16: 5160
- 6c Qin Z, Liu W, Wang D, He Z. J. Org. Chem. 2016; 81: 4690
- 6d Kang B, Lee MH, Kim M, Hwang J, Kim HB, Chi DY. J. Org. Chem. 2015; 80: 8254
- 6e Rahaman M, Hossain MM. Org. Synth. 2019; 96: 98
- 6f Sun P, Gao S, Yang С, Guo S, Lin A, Yao Н. Org. Lett. 2016; 18: 6464
- 6g Qin L, Vo D.-D, Nakhai A, Andersson CD, Elofsson M. ACS Comb. Sci. 2017; 19: 370
- 6h Sha Q, Liu H, Li Y. Adv. Synth. Catal. 2019; 361: 1627
- 6i Litvinova VA, Tikomirov AS. Chem. Heterocycl. Compd. 2019; 55: 689
- 7 Kundu D, Samim M, Majee A, Hajira A. Chem. Asian J. 2011; 6: 406
- 8 Revial G, Lim S, Viossat B, Lemoine P, Tomas A, Duprat AF, Pfau M. J. Org. Chem. 2000; 65: 4593
- 9a Ballini R, Fiorini D, Palmieri A. Tetrahedron Lett. 2004; 45: 7027
- 9b Palmieri A, Gabrielli S, Ballini R. Green Chem. 2013; 15: 2344