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DOI: 10.1055/a-2752-7750
A Concise and Sequential Synthetic Approach for Constructing [1,3]Oxazino[3,2‑a]indolyl Chalcones from 2-Oxindole
Authors
This work was financially supported by Vellore Institute of Technology (VIT), Vellore, under the Faculty Seed Grant (RGEMS), (VIT SEED GRANT No.: SG20250056).
Abstract
A base-promoted, transition-metal-free sequential synthesis of 3,4-dihydro-2H-oxazino[3,2-a]indole-10-carbaldehyde and its chalcone analogues is reported. The fused oxazinoindole framework was efficiently constructed from 2-chloro-1H-indole-3-carbaldehyde and 3-halopropanol through N-alkylation followed by intramolecular cyclization. Subsequent Claisen–Schmidt condensation of the resulting carbaldehyde with various substituted acetophenone derivatives under basic conditions afforded the corresponding chalcone analogues in good to excellent yields. All compounds were characterized by various spectroscopic techniques.
Keywords
N-Alkylindole - [1,3]Oxazino[3,2-a]indole - Chalcone - Claisen–Schmidt condensation - Intramolecular cyclizationPublication History
Received: 11 September 2025
Accepted after revision: 20 November 2025
Accepted Manuscript online:
20 November 2025
Article published online:
22 December 2025
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References
- 1 Santos AS, Raydan D, Cunha JC, Viduedo N, Silva AM, Marques MMB. Catalysts 2021; 11: 1108
- 2 Tyagi R, Yadav K, Khanna A, Mishra SK, Sagar R. Bioorg Med Chem 2024; 109: 117778
- 3a Xia Z, Wang K, Zheng J. et al. Org Biomol Chem 2012; 10: 1602
- 3b Osyanin VA, Klimochkin YN. Chem Heterocycl Compd 2009; 45: 833
- 4a Chen Z, Zeng X, Yan B, Zhao Y, Fu Y. RSC Adv 2015; 5: 100251
- 4b Deniz E, Tomasulo M, Sortino S, Raymo FM. J Phys Chem C 2009; 113: 8491
- 5a Bharath Kumar P, Raju CE, Roy S. et al. Org Lett 2024; 26: 8680
- 5b McComas CC, Palani A, Chang W. et al. ChemMedChem 2017; 12: 1436
- 6 Fedouloff M, Hossner F, Voyle M. et al. Bioorg Med Chem 2001; 9: 2119
- 7a Zagorskytė I, Arbačiauskienė E, Račkauskienė G. et al. RSC Adv 2025; 15: 18947
- 7b Buzard DJ, Schrader TO, Zhu X. et al. Bioorg Med Chem Lett 2015; 25: 659
- 8 An J, Chang NJ, Song LD. et al. Chem Commun 2011; 47: 1869
- 9 Palomba M, Vinti E, Marini F, Santi C, Bagnoli L. Tetrahedron 2016; 72 (44) 7059-7064
- 10 Vandavasi JK, Hu WP, Senadi GC, Boominathan SSK, Chen HY, Wang JJ. Eur J Org Chem 2014; 2014: 6219
- 11 Brudeli B, Moltzau LR, Nguyen CH. et al. Eur J Med Chem 2013; 64: 629
- 12 Wang XF, Cao WB, Li HY, Xu XP, Ji SJ. J Org Chem 2021; 86: 12597
- 13 Kumar KS, Kumar NP, Rajesham B, Kishan G, Akula S, Kancha RK. New J Chem 2018; 42: 34
- 14 Chen J, Zhong T, Zheng X. et al. Adv Synth Catal 2021; 363: 446
- 15a Preethi KR, Kannadasan S, Shanmugam P. ChemistrySelect 2024; 9: 202304705
- 15b Padmashrija AJC, Kannadasan S, Shanmugam P. ChemistrySelect 2023; 8: 202302522
- 16 King FD, Gaster LM, Mulholland KR. 5-HT₄ Receptor Antagonists, WO 94/27987 1994