ARTICLES

Synthesis of Benzochromenes via Brønsted Acid Catalyzed Annulation of Naphthol with Propargyl Alcohols

  • Pin Zhao ,
  • Xuwei Shang ,
  • Qingqing Luo ,
  • Mengyu Liang ,
  • Yuan Fu ,
  • Mingliang Zhang ,
  • Lantao Liu
Expand
  • a College of Chemistry, Zhengzhou University, Zhengzhou 450001
    b Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000

Received date: 2023-12-13

  Revised date: 2024-02-23

  Online published: 2024-03-13

Supported by

National Natural Sciences Foundation of China(21572126); National Natural Sciences Foundation of China(21901152); Key Scientific and Technological Project of Henan Province(202102310003); Leading Talent Funding Project of Shangqiu Talent Support Plan in Henan Province(SQRC202212004)

Abstract

Benzeochromenes, also named as naphthopyrans, are widely found in natural products, bioactive molecules and organic functional materials. A simple and efficient strategy for the synthesis of benzeochromenes with propargyl alcohols and β-naphthols under mild conditions was developed, and a series of benzeochromenes were prepared in excellent yields. This protocol has the advantages of broad scope, functional group diversity and mild conditions with H2O as the only byproduct. Moreover, ease of operation and gram-scale preparation portend the practical application.

Cite this article

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 . DOI: 10.6023/cjoc202312012

References

[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.
[1]
(b) Singh, R.; Geetanjali, G.; Chauhan, S. M. S. Chem. Biodiversity 2004, 1, 1241.
[1]
(c) Marec, F.; Kollarova, I.; Jegorov, A. Planta Med. 2001, 67,127.
[1]
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.
[1]
(e) Endale, M.; Ekberg, A.; Akala, H. M.; Alao, J. P.; Sunnerhagen, P.; Yenesew, A.; Erdélyi, M. J. Nat. Prod. 2012, 75, 1299.
[1]
(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.
[1]
(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.
[1]
(h) Chin, Y.-W.; Yoon, K. D.; Kim, J. Anti-Cancer Agents Med. Chem. 2009, 9, 913.
[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.
[2]
(b) Azab, I. H. E.; Break, L. M.; El-Zahrani, Z. A. A. Orient. J. Chem. 2016, 32, 2435.
[2]
(c) Mercaldi, G. F.; D'Antonio, E. L.; Aguessi, A.; Rodriguez, A.; Cordeiro, A. T. Bioorg. Med. Chem. Lett. 2019, 29, 1948.
[2]
(d) Fu, Z.-Y.; Jin, Q.-H.; Qu, Y.-L.; Guan, L.-P. Bioorg. Med. Chem. Lett. 2019, 29, 1909.
[2]
(e) Galano, J. J.; Alias, M.; Perez, R.; Velazquez-Campoy, A.; Hoffman, P. S.; Sancho, J. J. Med. Chem. 2013, 56, 6248.
[2]
(f) Nicolaou, K. C.; Evans, R. M; Roecker, A. J.; Hughes, R.; Downes, M.; Pfefferkorn, J. A. Org. Biomol. Chem. 2003, 1, 908.
[2]
(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.
[3]
(a) Kaneko, T.; Akutsu, H.; Yamada, J.; Nakatsuji, S. Org. Lett. 2003, 5, 2127.
[3]
(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.
[3]
(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.
[4]
(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.
[4]
(c) Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. J. Chin. Chem. Soc. 2008, 55, 659.
[4]
(d) Saikia, M.; Saikia, L. RSC Adv. 2016, 6, 15846.
[4]
(e) Khurana, J. M.; Nand, B.; Saluja, P. Tetrahedron 2010, 66, 5637.
[4]
(f) Aghajani, M.; Monadi, N. J. Chin. Chem. Soc. 2019, 66, 775.
[4]
(g) Fekri, L. Z.; Barazandehdoust, M. Polycycl. Aromat. Compd. 2021, 41, 2074.
[5]
(a) Kundu, S. K.; Mondal, J.; Bhaumik, A. Dalton Trans. 2013, 42, 10515.
[5]
(b) Safari, J.; Zarnegar, Z.; Heydarian, M. Bull. Chem. Soc. Jpn. 2012, 85, 1332.
[5]
(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.
[7]
(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.
[8]
(b) Zarnegar, Z.; Safari, J. New J. Chem. 2016, 40, 7986.
[8]
(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)
[11]
(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.
[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.; Tr?ber, 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)
[19]
(刘静, 陈锦涛, 刘婷婷, 刘佳, 曾要富, 有机化学, 2023, 43, 379.)
[20]
(a) Du, S.; Zhou, A.-X.; Yang, R.; Song, X.-R.; Xiao, Q. Org. Chem. Front. 2021, 8, 6760.
[20]
(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.
Outlines

/