One-pot Two-step Reaction for Synthesis of Poly-substituted Pyrano[3,2-c]pyridones and Spiro[indoline-3,4′-pyrano[3,2-c]pyridine]-2,5′(6′H)-diones in Water
Zhenhang Xu
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorYijun Du
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorSongxiang Wang
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorZeru Wu
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorYuhao Lou
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorCorresponding Author
Furen Zhang
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
E-mail: [email protected]Search for more papers by this authorZhenhang Xu
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorYijun Du
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorSongxiang Wang
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorZeru Wu
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorYuhao Lou
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
Search for more papers by this authorCorresponding Author
Furen Zhang
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province, 312000 China
E-mail: [email protected]Search for more papers by this authorAbstract
An efficient four-component approach for the synthesis poly-substituted pyrano[3,2-c]pyridones and spiro[indoline-3,4′-pyrano[3,2-c]pyridine]-2,5′(6′H)-diones in water has been established. During the reaction, the products were readily achieved through one-pot two-step reaction using solid acid as catalyst. The advantages of atom and step economy, the recyclability of heterogeneous solid acid catalyst, easy workup procedure, and the wide scope of substrates make the reaction a powerful tool for assembling pyrano[3,2-c]pyridone skeletons of chemical and medical interest.
Supporting Information
Filename | Description |
---|---|
jhet3646-sup-0001.docxWord 2007 document , 3.5 MB |
Data S1. Supporting information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References and Notes
- 1(a) Rueping, M.; Sugiono, E.; Merino, E. Chem A Eur J 2008, 14, 6329; (b) Mohareb, R. M.; Schatz, J. Bioorg Med Chem 2011, 19, 2707; (c) Davarpanah, J.; Kiasat, A. R.; Noorizadeh, S.; Ghahremani, M. J Mol Catal A Chem 2013, 376, 78; (d) Beerappa, M.; Shivashankar, K. RSC Adv 2015, 5, 30364.
- 2Parthasarathy, K.; Praveen, C.; Balachandran, C.; Senthil Kumar, P.; Ignacimuthu, S.; Perumal, P. T. Bioorg Med Chem Lett 2013, 23, 2708.
- 3(a) Sakhuja, R.; Panda, S. S.; Khanna, L.; Khurana, S.; Jain, S. C. Bioorg Med Chem Lett 2011, 21, 5465; (b) Raj, T.; Bhatia, R. K.; Kapur, A.; Sharma, M.; Saxena, A. K.; Ishar, M. P. S. Eur J Med Chem 2010, 45, 790.
- 4(a) Kumar, N. V.; Rajendran, S. P. Asian J Chem 2004, 16, 1911; (b) Hanawa, F.; Fokialakis, N.; Skaltsounis, A. L. Planta Med 2004, 70, 531; (c) Fujita, Y.; Oguri, H.; Oikawa, H. J Antibiot 2005, 58, 425.
- 5Cantrell, C. L.; Schrader, K. K.; Mamonov, L. K.; Sitpaeva, G. T.; Kustova, T. S.; Dunbar, C.; Wedge, D. E. J Agric Food Chem 2005, 53, 7741.
- 6Chen, J. J.; Chen, P. H.; Liao, C. H.; Huang, S. Y.; Chen, I. S. J Nat Prod 2007, 70, 1444.
- 7Fan, X.; Feng, D.; Qu, Y.; Zhang, X.; Wang, J.; Loiseau, P. M.; Andrei, G.; Snoeck, R.; Clercq, E. D. Bioorg Med Chem Lett 2010, 20, 809.
- 8(a) McBrien, K. D.; Gao, Q.; Huang, S.; Klohr, S. E.; Wang, R. R.; Pirnik, D. M. J Nat Prod 1996, 59, 1151; (b) Kamperdick, C.; Van, N. H.; Van Sung, T.; Adam, G. Phytochemistry 1999, 50, 177.
- 9(a) Tatsuta, K.; Yamaguchi, T.; Tsuda, Y.; Yamaguchi, Y.; Hattori, N.; Nagai, H.; Hosokawa, S. Tetrahedron Lett 2007, 48, 4187; (b) Chen, I. S.; Wu, S. J.; Tsai, I. L.; Wu, T. S.; Pezzuto, J. M.; Lu, M. C.; Chai, H.; Suh, N.; Teng, C. M. J Nat Prod 1994, 57, 1206; (c) Brahmachari, G.; Banerjee, B. ACS Sustainable Chem Eng 2014, 2, 411.
- 10(a) Baghbanian, S. M. RSC Adv 2014, 4, 59397; (b) Seifi, M.; Sheibani, H. Catal Lett 2008, 126, 275; (c) Elinson, M. N.; Ryzhkov, F. V.; Vereshchagin, A. N.; Zaimovskaya, T. A.; Korolev, V. A.; Egorov, M. P. Mendeleev Commun 2016, 26, 399; (d) Stoyanov, E. V.; Ivanov, I. C.; Heber, D. Molecules 2000, 5, 19; (e) Abbaspour-Gilandeh, E.; Aghaei-Hashjin, M.; Yahyazadeh, A.; Salemi, H. RSC Adv 2016, 6, 55444.
- 11Suganuma, S.; Nakajima, K.; Kitano, M.; Yamaguchi, D.; Kato, H.; Hayashi, S.; Hara, M. Solid State Sci 2010, 12, 1029.
- 12(a) Margelefsky, E. L.; Bendjériou, A.; Zeidan, R. K.; Dufaud, V.; Davis, M. E. J Am Chem Soc 2008, 130, 13442; (b) Ziarani, G. M.; Lashgari, N.; Badiei, A. J Mol Catal A Chem 2015, 397, 166; (c) Rostamnia, S.; Xin, H.; Liu, X.; Lamei, K. J Mol Catal A Chem 2013, 85, 374; (d) Bispo, C.; Ferreira, P.; Trouvé, A.; Batonneau-Gener, I.; Liu, F.; Jérôme, F.; Bion, N. Catal Today 2013, 85, 218; (e) Wang, L.-M.; Jiao, N.; Qiu, J.; Yu, J.-J.; Liu, J.-Q.; Guo, F.-L.; Liu, Y. Tetrahedron 2010, 66, 339; (f) Ziarani, G. M.; Mousavi, S.; Lashgari, N.; Badiei, A. J Chem Sci 2013, 125, 1359.
- 13(a) Li, C. M.; Liang, X. Z.; Zhang, F. R.; Qi, C. Z. Cat Com 2015, 62, 6; (b) Zhang, F. R.; Li, C. M.; Wang, C.; Qi, C. Z. Org Biomol Chem 2015, 13, 5022; (c) Chen, Z.; Shi, Y. X.; Shen, Q. Q.; Xu, H. X.; Zhang, F. R. Tetrahedron Lett 2015, 56, 4749; (d) Zhang, F. R.; Li, C. M.; Liang, X. Z. Green Chem 2018, 20, 2057.
- 14Liang, X. Z.; Zeng, M. F.; Qi, C. Z. Carbon 2010, 48, 1844.