Continuous Flow Telescoped Synthesis of Benzofurans Starting from Nitroalkanes and O-Acetyl Salicylaldehydes

Marino Petrini; Alessandro Palmieri; Elettra Gheco

doi:10.1055/a-2642-4294

Synthesis, Table of Contents

Synthesis 2025; 57(21): 3361-3369
DOI: 10.1055/a-2642-4294

Paper

Published as part of the Special Topic Dedicated to Prof. Paul Knochel

Continuous Flow Telescoped Synthesis of Benzofurans Starting from Nitroalkanes and O-Acetyl Salicylaldehydes

Authors

Marino Petrini

Green Chemistry Group, School of Sciences and Technology, Chemistry Division, University of Camerino, Camerino, Italy
Alessandro Palmieri

Green Chemistry Group, School of Sciences and Technology, Chemistry Division, University of Camerino, Camerino, Italy
Elettra Gheco

Green Chemistry Group, School of Sciences and Technology, Chemistry Division, University of Camerino, Camerino, Italy

Abstract

All articles of this category

Dedication

Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.

Abstract

Herein, we report a new practical flow chemical synthesis of benzofurans starting from nitroalkanes and O-acetyl salicylaldehydes. The protocol involves two different sequential steps: (i) an initial base-promoted nitroaldol condensation, and (ii) a Nef reaction promoted by tin (II) chloride dihydrate. The target benzofurans are obtained in satisfactory overall yields.

Keywords

Flow chemistry - Benzofurans - Nitroalkanes - Cyclization - Heterocycles

Full Text

References

References

1a Arce-Ramos L, Castillo J-C, Becerra D. Pharmaceuticals 2023; 16: 1265
1b Miao Y, Hu Y, Yang J, Liu T, Sun J, Wang X. RSC Adv 2019; 9: 27510
1c Heravi MM, Zadsirjan V, Hamidi H, Amiri PHT. RSC Adv 2017; 7: 24470
1d Khanam H. Shamsuzzaman Eur J Med Chem 2015; 97: 483

2a Mushtaq A, Zahoor AF, Ahmad S. et al. ACS Omega 2024; 9: 20728
2b Dwarakanath D, Gaonkar SL. Asian J Org Chem 2022; 11: e202200282

3a Jin R, Wang L, Song Y, Liu X, Wang J, Li Z. Chin J Org Chem 2024; 44: 2742
3b Chiummiento L, D’Orsi R, Funicello M, Luppatelli P. Molecules 2020; 25: 2327

4a Ghosh M, Santra S, Mondal P, Kundu D, Hajra A. Chem Asian J 2015; 10: 2525
4b Kumar T, Mobin SM, Namboothiri INN. Tetrahedron 2013; 69: 4964
4c Kundu D, Samim M, Majee A, Hajra A. Chem Asian J 2011; 6: 406

5 Bassetti B, Principi M, Ballini R, Petrini M, Palmieri A. Synthesis 2024; 56: 3167
6 For a review on the Nef reaction see: Ballini R, Petrini M. Adv Synth Catal 2015; 357: 2371

7a Grishin IY, Arutiunov NA, Aksenov DA. et al. Molecules 1902; 2022: 27
7b Han X, Ye C, Chen F, Chen Q, Wang Y, Zeng X. Org Biomol Chem 2017; 15: 3401

8 Huang C-Y, Kuo C-W, Kavala V, Yao C-F. Eur J Org Chem 2016; 2016: 2720
9 Bassetti B, Wang L, Ballini R, Petrini M, Palmieri A. Synthesis 2024; 56: 3615
10 Khan MEI, Lighuen Cassini T, Petrini M, Palmieri A. Org Biomol Chem 2024; 22: 3299

For the concept of “space integration of reactions” see:

11 Yoshida J, Saito K, Nokami T, Nagaki A. Synlett 2011; 2011: 1189

12a Hone CA, Kappe CO. Chem Methods 2021; 1: 454
12b Plutschack MB, Pieber B, Gilmore K, Seeberger PH. Chem Rev 2017; 117: 11796
12c Born S, O’Neal E, Jensen KF. In Comprehensive Organic Synthesis II. Knochel P, Molander GA. edsVol 9. Amsterdam: Elsevier; 2014: 54
12d Baxendale IR, Ley SV. Chimia 2008; 62: 162

13a Capaldo L, Wen Z, Noël T. Chem Sci 2023; 14: 4230
13b Dallinger D, Kappe CO. Curr Opin Green Sustainable Chem 2017; 7: 6
13c Porta R, Benaglia M, Puglisi A. Org Process Res Dev 2016; 20: 2

14a Jorea A, Bassetti B, Gervasoni K, Protti S, Palmieri A, Ravelli D. Adv Synth Catal 2023; 365: 722
14b Chiurchiù E, Sampaolesi S, Allegrini P, Ciceri D, Ballini R, Palmieri A. Eur J Org Chem 2021; 2021: 1286
14c Chiurchiù E, Patehebieke Y, Gabrielli S, Ballini R, Palmieri A. Adv Synth Catal 2019; 361: 2042
14d Chiurchiù E, Palmieri A, Petrini M. ARKIVOC 2019; iv: 69

15 https://www.uniqsis.com/paProductsDetail.aspx?ID=FlowLab

16a Sedelmeier J, Ley SV, Baxendale IR, Baumann M. Org Lett 2010; 12: 3618
16b Agalave SG, Chaudhari MB, Bisht GS, Gnanaprakasam B. ACS Sustainable Chem Eng 2018; 6: 12845

17 Kayakiri H, Abe Y, Hamashima H. et al. US 6348474B1 2002
18 Friedman MR, Toyne KJ, Goodby JW, Hird M. J Mater Chem 2011; 11: 2759-2772
19 Zhou L, Shi Y, Xiao Q. et al. Org Lett 2011; 13: 968-971
20 Gritti A, Brambilla E, Nania I, Turba F, Pirovano V, Abbiati G. Org Biomol Chem 2024; 22: 7895-7904
21 Yao J, Xiao Y, Li H. et al. Org Lett 2024; 26: 7307-7312

Supplementary Material

Supplementary Material (PDF)