Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1920-1928.DOI: 10.6023/cjoc202312012 Previous Articles Next Articles
ARTICLES
赵聘a, 尚旭伟b, 罗清清b, 梁梦雨b, 符媛b, 张明亮b,*(), 刘澜涛a,b,*()
收稿日期:
2023-12-13
修回日期:
2024-02-23
发布日期:
2024-03-12
基金资助:
Pin Zhaoa, Xuwei Shangb, Qingqing Luob, Mengyu Liangb, Yuan Fub, Mingliang Zhangb,*(), Lantao Liua,b,*()
Received:
2023-12-13
Revised:
2024-02-23
Published:
2024-03-12
Contact:
* E-mail: Supported by:
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Pin Zhao, Xuwei Shang, Qingqing Luo, Mengyu Liang, Yuan Fu, Mingliang Zhang, Lantao Liu. Synthesis of Benzochromenes via Brønsted Acid Catalyzed Annulation of Naphthol with Propargyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1920-1928.
Entry | Cat. | Solvent | Yield b/% |
---|---|---|---|
1 | (PhO)2PO2H | DCM | 47 |
2 | TsOH | DCM | 98 |
3 | H3PO4 | DCM | 23 |
4 | PhCO2H | DCM | Trace |
5 | AcOH | DCM | Trace |
6 | TsOH | EtOAc | N.d. |
7 | TsOH | THF | Trace |
8 | TsOH | CH3CN | 59 |
9 | TsOH | Toluene | 90 |
10c | TsOH | DCM | 79 |
11d | TsOH | DCM | 81 |
12e | TsOH | DCM | 95 |
13f | TsOH | DCM | 77 |
14g | TsOH | DCM | 84 |
Entry | Cat. | Solvent | Yield b/% |
---|---|---|---|
1 | (PhO)2PO2H | DCM | 47 |
2 | TsOH | DCM | 98 |
3 | H3PO4 | DCM | 23 |
4 | PhCO2H | DCM | Trace |
5 | AcOH | DCM | Trace |
6 | TsOH | EtOAc | N.d. |
7 | TsOH | THF | Trace |
8 | TsOH | CH3CN | 59 |
9 | TsOH | Toluene | 90 |
10c | TsOH | DCM | 79 |
11d | TsOH | DCM | 81 |
12e | TsOH | DCM | 95 |
13f | TsOH | DCM | 77 |
14g | TsOH | DCM | 84 |
[1] |
(a) Costa, S. M.O.; Lemos, T. L. G.; Pessoa, O. D. L.; Pessoa, C.; Montenegro, R. C.; Braz, F. R. J. Nat. Prod. 2001, 64, 792.
pmid: 15043429 |
(b) Singh, R.; Geetanjali, G.; Chauhan, S. M. S. Chem. Biodiversity 2004, 1, 1241.
pmid: 15043429 |
|
(c) Marec, F.; Kollarova, I.; Jegorov, A. Planta Med. 2001, 67,127.
pmid: 15043429 |
|
Chung, M. I.; Jou, S. J.; Cheng, H, C.; Lin, C. N.; Ko, F. N.; Teng, C. M. (d) Chung, M. I.; Jou, S. J.; Cheng, H, C.; Lin, C. N.; Ko, F. N.; Teng, C. M. J. Nat. Prod. 1994, 57, 313.
pmid: 15043429 |
|
(e) Endale, M.; Ekberg, A.; Akala, H. M.; Alao, J. P.; Sunnerhagen, P.; Yenesew, A.; Erdélyi, M. J. Nat. Prod. 2012, 75, 1299.
pmid: 15043429 |
|
(f) Hussein, A. A.; Barberena, I.; Capson, T. L.; Kursar, T. A.; Coley, P. D.; Solis, P. N.; Gupta, M. P. J. Nat. Prod. 2004, 67, 451.
pmid: 15043429 |
|
(g) Bukuru, J. F.; Van, T. N.; Puyvelde, L. V.; Mathenge, S. G.; Mudida, F. P.; Kimpe, N. D. J. Nat. Prod. 2004, 65, 783.
pmid: 15043429 |
|
(h) Chin, Y.-W.; Yoon, K. D.; Kim, J. Anti-Cancer Agents Med. Chem. 2009, 9, 913.
pmid: 15043429 |
|
[2] |
For selected reviews, see: (a) Tan, Q.-W.; He, L.-Y.; He, Z.-W.; Liu, W.-H.; Zhang, S.-S.; Lin, L.; Yang, H.-L.; Guan, L.-P. Med. Chem. Res. 2021, 30, 1427.
pmid: 9804685 |
(b) Azab, I. H. E.; Break, L. M.; El-Zahrani, Z. A. A. Orient. J. Chem. 2016, 32, 2435.
pmid: 9804685 |
|
(c) Mercaldi, G. F.; D'Antonio, E. L.; Aguessi, A.; Rodriguez, A.; Cordeiro, A. T. Bioorg. Med. Chem. Lett. 2019, 29, 1948.
doi: S0960-894X(19)30334-8 pmid: 9804685 |
|
(d) Fu, Z.-Y.; Jin, Q.-H.; Qu, Y.-L.; Guan, L.-P. Bioorg. Med. Chem. Lett. 2019, 29, 1909.
pmid: 9804685 |
|
(e) Galano, J. J.; Alias, M.; Perez, R.; Velazquez-Campoy, A.; Hoffman, P. S.; Sancho, J. J. Med. Chem. 2013, 56, 6248.
doi: 10.1021/jm400786q pmid: 9804685 |
|
(f) Nicolaou, K. C.; Evans, R. M; Roecker, A. J.; Hughes, R.; Downes, M.; Pfefferkorn, J. A. Org. Biomol. Chem. 2003, 1, 908.
pmid: 9804685 |
|
(g) Marot, C.; Chavatte, P.; Morin-Allory, L.; Viaud, M. C.; Guillaumet, G.; Renard, P.; Lesieur, D.; Michel, A. J. Med. Chem. 1998, 41, 4453.
pmid: 9804685 |
|
[3] |
(a) Kaneko, T.; Akutsu, H.; Yamada, J.; Nakatsuji, S. Org. Lett. 2003, 5, 2127.
|
(b) Ushakov, E. N.; Nazarov, V. B.; Fedorova, O. A.; Gromov, S. P.; Chebun'kova, A. V.; Alfimov, M. V.; Barigelletti, F. J. Phys. Org. Chem. 2003, 16, 306.
|
|
(c) Guo, K.; Chen, Y. Mol. Cryst. Liq. Cryst. 2009, 501, 62.
|
|
[4] |
(a) Shinde, S.; Rashinkar, G.; Salunkhe, R. J. Mol. Liq. 2013, 178,122.
pmid: 16143530 |
(b) Kemnitzer, W.; Kasibhatla, S.; Jiang, S. H.; Zhang, H.; Zhao, J. H.; Jia, S. J.; Xu, L. F.; Crogan-Grundy, C.; Denis, R.; Barriault, N.; Vaillancourt, L.; Charron, S.; Dodd, J.; Attardo, G.; Labrecque, D.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Drewe, J.; Cai, S. X. Bioorg. Med. Chem. Lett. 2005, 15, 4745.
pmid: 16143530 |
|
(c) Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. J. Chin. Chem. Soc. 2008, 55, 659.
pmid: 16143530 |
|
(d) Saikia, M.; Saikia, L. RSC Adv. 2016, 6, 15846.
pmid: 16143530 |
|
(e) Khurana, J. M.; Nand, B.; Saluja, P. Tetrahedron 2010, 66, 5637.
pmid: 16143530 |
|
(f) Aghajani, M.; Monadi, N. J. Chin. Chem. Soc. 2019, 66, 775.
pmid: 16143530 |
|
(g) Fekri, L. Z.; Barazandehdoust, M. Polycycl. Aromat. Compd. 2021, 41, 2074.
pmid: 16143530 |
|
[5] |
(a) Kundu, S. K.; Mondal, J.; Bhaumik, A. Dalton Trans. 2013, 42, 10515.
|
(b) Safari, J.; Zarnegar, Z.; Heydarian, M. Bull. Chem. Soc. Jpn. 2012, 85, 1332.
|
|
(c) Ren, Y.-M.; Cai, C. Catal. Commun. 2008, 9, 1017.
|
|
[6] |
Eshghi, H. Damavandi, S.; Zohuri, G. H. Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 2011, 41, 1067.
|
[7] |
(a) Fareghi-Alamdari, R.; Zekri, N.; Mansouri, F. Res. Chem. Intermed. 2017, 43, 6537.
|
(b) Kumar, D.; Reddy, V. B.; Mishra, B. G.; Rana, R, K.; Nadagouda, M, N.; Varma, R.S. Tetrahedron 2007, 63, 3093.
|
|
[8] |
(a) Mayank.; Billing, B. K.; Agnihotri, P. K.; Kaur, N.; Singh, N.; Jang, D. O. ACS Sustainable Chem. Eng. 2018, 6, 3714.
|
(b) Zarnegar, Z.; Safari, J. New J. Chem. 2016, 40, 7986.
|
|
(c) Zhu, A.; Li, Q.; Feng, W.; Fan, D.; Li, L. Catal. Lett. 2021, 151, 720.
|
|
[9] |
Pawar, G. T.; Magar, R. R.; Lande, M. K. Polycyclic Aromat. Compd. 2016, 38, 75.
|
[10] |
Yin, G. D.; Fan, L. F.; Ren, T. B.; Zheng, C. Y.; Tao, Q.; Wu, A. X.; She, N. F. Org. Biomol. Chem. 2012, 10, 8877.
|
[11] |
Shi, D.; Zhang, S.; Zhuang, Q.; Wang, X.; Tu, S.; Hu, H. Chin. J. Org. Chem. 2003, 23, 1419. (in Chinese)
|
(史达清, 张姝, 庄启亚, 王香善, 屠树江, 胡宏纹, 有机化学, 2003, 23, 1419.)
|
|
[12] |
Sreenivasulu, C.; Thadathil, D. A.; Pal, S.; Gedu, S. Synth. Commun. 2020, 50, 112.
|
[13] |
Porno, J.-L.; Samat, A.; Guglielmetti, R.; Dubest, R.; Aubard, J. Helv. Chim. Acta 1997, 80, 725.
|
[14] |
Tanaka, K.; Aoki, H.; Hosomi, H.; Ohb, S. Org. Lett. 2000, 2, 2133.
pmid: 10891248 |
[15] |
McCubbin, J. A.; Nassar, C.; Krokhin, O. V. Synthesis 2011, 19, 3152.
|
[16] |
Yaragorla, S.; Pareek, A.; Dada, R. Tetrahedron Lett. 2017, 58, 4642.
|
[17] |
Kahle, I.; Tröber, O.; Richter, H.; Spange, S. New J. Chem. 2013, 37, 1479.
|
[18] |
Zhang, X.-Z.; Li, B. Q.; Qiu, Z.-W.; Ma, A.; Peng, J.; Du, J.-Y.; Feng, N.; Xu, X.-T.; Pan, H.-P. J. Org. Chem. 2020, 85, 13306.
|
[19] |
Liu, J.; Chen, J.; Liu, T.; Liu, J.; Zeng, Y. Chin. J. Org. Chem. 2023, 43, 379. (in Chinese)
|
(刘静, 陈锦涛, 刘婷婷, 刘佳, 曾要富, 有机化学, 2023, 43, 379.)
doi: 10.6023/cjoc202207015 |
|
[20] |
(a) Du, S.; Zhou, A.-X.; Yang, R.; Song, X.-R.; Xiao, Q. Org. Chem. Front. 2021, 8, 6760.
|
(b) Qian, H.; Huang, D.; Bi, Y.; Yan, G. Adv. Synth. Catal. 2019, 361, 3240.
|
|
[21] |
Yaragorla, S.; Rajesh, P.; Pareek, A.; Kumar, A. Adv. Synth. Catal. 2018, 360, 4422.
|
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