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 2024; 56(20): 3199-3205
DOI: 10.1055/s-0043-1775386
DOI: 10.1055/s-0043-1775386
paper
Regio- and Chemoselective Synthesis of 4,6-Dithia-1,2,9-triazaspiro[4.4]non-2-en-8-ones through an Ultrasound-Promoted One-Pot Sequential Pseudo-Five-Component Reaction
We are grateful to the Research Council of Tarbiat Modares University for supporting this work.
Abstract
Spiro-heterocycles have attracted significant interest due to their unique biological properties with fewer side effects compared to traditional drugs. Herein, a novel method is reported for the synthesis of a series of spiro-heterocycles possessing a quinoline motif. The strategy utilizes rhodanine derivatives, hydrazonoyl chlorides, and 2-chloroquinoline-3-carbaldehyde, and proceeds via a one-pot sequential pseudo-five-component reaction. The reactions are found to proceed in a regioselective and chemoselective manner.
Key words
rhodanine - hydrazonoyl chlorides - 2-chloroquinoline-3-carbaldehyde - 4,6-dithia-1,2,9-triazaspiro[4.4]non-2-en-8-ones - five-component reaction - regioselective - chemoselective - ultrasoundSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775386.
- Supporting Information
Publication History
Received: 21 January 2024
Accepted after revision: 03 July 2024
Article published online:
22 July 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565
- 2 The Chemistry of Heterocyclic Compounds: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Vol. 59. Padwa A, Pearson WH. John Wiley & Sons; New York: 2003
- 3 Nair V, Suja T. Tetrahedron 2007; 63: 12247
- 4 Liu H, Dou G, Shi D. J. Comb. Chem. 2010; 12: 633
- 5 Rajesh SM, Bala BD, Perumal S. Tetrahedron Lett. 2012; 53: 5367
- 6 Borad MA, Bhoi MN, Prajapati NP, Patel HD. Synth. Commun. 2014; 44: 897
- 7 Martina K, Tagliapietra S, Veselov VV, Cravotto G. Front. Chem. 2019; 7: 95
- 8 Breugst M, Reissig H.-U. Angew. Chem. Int. Ed. 2020; 59: 12293
- 9 Maiuolo L, Algieri V, Olivito F, De Nino A. Catalysts 2020; 10: 65
- 10 Thakur S, Das A, Das T. New J. Chem. 2021; 45: 11420
- 11 Behera RK, Behera AK, Pradhan R, Pati A, Patra M. Synth. Commun. 2006; 36: 3729
- 12 Arya AK, Kumar M. Green Chem. 2011; 13: 1332
- 13 Mohamed Teleb MA, Kamel MG, Ead HA, Hassaneen HM, Saleh FM. Polycyclic Aromat. Compd. 2023; 43: 572
- 14 Saraswat P, Jeyabalan G, Hassan MZ, Rahman MU, Nyola NK. Synth. Commun. 2016; 46: 1643
- 15 Senthil Kumar G, Satheeshkumar R, Kaminsky W, Platts J, Rajendra Prasad KJ. Tetrahedron Lett. 2014; 55: 5475
- 16 Arumugam N, Suresh Kumar R, Almansour AI, Perumal S. Curr. Org. Chem. 2013; 17: 1929
- 17 Nainwal LM, Tasneem S, Akhtar W, Verma G, Khan MF, Parvez S, Shaquiquzzaman M, Akhter M, Alam MM. Eur. J. Med. Chem. 2019; 164: 121
- 18 Matada BS, Pattanashettar R, Yernale NG. Bioorg. Med. Chem. 2021; 32: 115973
- 19 Kumar S, Bawa S, Gupta H. Mini-Rev. Med. Chem. 2009; 9: 1648
- 20 Afzal O, Kumar S, Haider MR, Ali MR, Kumar R, Jaggi M, Bawa S. Eur. J. Med. Chem. 2015; 97: 871
- 21 Solomon VR, Lee H. Curr. Med. Chem. 2011; 18: 1488
- 22 Subhedar DD, Shaikh MH, Shingate BB, Nawale L, Sarkar D, Khedkar VM, Kalam Khan FA, Sangshetti JN. Eur. J. Med. Chem. 2017; 125: 385
- 23 Dawood KM, Farghaly TA. Expert Opin. Ther. Pat. 2017; 27: 477
- 24 Bhuva H, Sahu D, Shah B, Modi DC, Patel MB. Pharmacologyonline 2011; 1: 528
- 25 Li Y, Geng J, Liu Y, Yu S, Zhao G. Chem. Med. Chem. 2013; 8: 27
- 26 Pandey Y, Singh A, Sharma PK, Kumar N. J. Curr. Pharma Res. 2011; 1: 192
- 27 Jain VS, Vora DK, Ramaa CS. Bioorg. Med. Chem. 2013; 21: 1599
- 28 Asati V, Mahapatra DK, Bharti SK. Eur. J. Med. Chem. 2014; 87: 814
- 29 Jain AK, Sharma S, Vaidya A, Ravichandran V, Agrawal RK. Chem. Biol. Drug Des. 2013; 81: 557
- 30 Szeliga M. Pharmacol. Rep. 2020; 72: 1079
- 31 Havrylyuk D, Roman O, Lesyk R. Eur. J. Med. Chem. 2016; 113: 145
- 32 Bajpai P, Jain S, Choubey A. Asian J. Res. Chem. 2020; 13: 283
- 33 Desai NC, Rupala YM, Khasiya AG, Shah KN, Pandit UP, Khedkar VM. J. Heterocycl. Chem. 2022; 59: 75
- 34 Alizadeh A, Roosta A, Rezaiyehrad R, Halvagar M. Tetrahedron 2017; 73: 6706
- 35 Alizadeh A, Rezaiyehraad R, Roosta A, Halvagar MR. ChemistrySelect 2019; 4: 12049
- 36 Alizadeh A, Roosta A, Rezaiyehraad R. J. Iran. Chem. Soc. 2020; 17: 1123
- 37 Alizadeh A, Jamal P, Roosta A, Rezaiyehraad R, Liu T.-F, Khanpour M. Mol. Diversity 2021; 25: 701
- 38 Alizadeh A, Hosseini SY, Sedighian H, Bayat F. Helv. Chim. Acta 2015; 98: 1426
- 39 Alizadeh A, Moafi L. Heterocycl. Commun. 2017; 23: 375
- 40 Alizadeh A, Roosta A, Amir Ashjaee Asalemi K. J. Sulfur Chem. 2018; 39: 435
- 41 Alizadeh A, Roosta A, Halvagar M. ChemistrySelect 2019; 4: 71
- 42 Roosta A, Alizadeh A, Rezaiyehraad R, Khanpour M. ChemistrySelect 2020; 5: 12531
- 43 Hassaneen HM, Shawali AS, Farag DS, Ahmed EM. Phosphorus, Sulfur Silicon Relat. Elem. 1996; 113: 53
- 44 Hassaneen HM, Abunada NM, Miqdad OA, Fares AA. Asian J. Chem. 2012; 24: 330
- 45 Hassaneen HM, Shawali AS, Saleh FM. J. Sulfur Chem. 2016; 37: 241