A New Approach to the Synthesis of Bergapten

doi:10.1007/s40242-022-2089-7

Chemical Research in Chinese Universities ›› 2022, Vol. 38 ›› Issue (6): 1492-1496.doi: 10.1007/s40242-022-2089-7

• Articles • Previous Articles Next Articles

A New Approach to the Synthesis of Bergapten

CAI Xiaoqing¹, JI Dongxin², LIU Jiageng³, HU Maolin¹, JIN Zhimin²

1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China;
2. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China;
3. Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China

Received:2022-03-11 Online:2022-12-01 Published:2022-12-06
Contact: JIN Zhimin E-mail:apharm@sina.com
Supported by:
This work was supported by the Project of Department of Science and Technology of Zhejiang Province, China(No.2021C04021).

Abstract

Abstract: In this study, bergapten was synthesized in a yield of 55% from phloroglucinol as starting material, via a novel approach including monomethylation, Hoesch reaction, acetylation, deacetoxylation, Pechmann condensation and 2,3-dichloro-5,6- dicyano-1,4-benzoquinone(DDQ) dehydrogenation. With the adoption of the acetylation of enol tautomer, the deacetoxylation and the DDQ dehydrogenation, the novel approach differs greatly from the processes reported previously, though the starting material was the same or similar to those used on previous synthetic processes. The newly adopted reaction underwent easily, affording all reactions in high yields, especially acetylation and deacetoxylation and DDQ dehydrogenation in almost quantitative yields, ensuring a final yield higher than those previously reported.

Key words: Bergapten, Enol tautomerism, Acetylation, Deacetoxylation, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) dehydrogenation

CAI Xiaoqing, JI Dongxin, LIU Jiageng, HU Maolin, JIN Zhimin. A New Approach to the Synthesis of Bergapten[J]. Chemical Research in Chinese Universities, 2022, 38(6): 1492-1496.

References

[1] Panno M. L., Giordano F., Palma M. G., Bartella V., Rago V., Maggiolini M., Sisci D., Lanzino M., de Amicis F., Ando S., Curr. Cancer Drug Tar., 2009,9(4), 469;
[2] Lee Y. M., Wu T. H., Chen S. F., Chung J. G., Toxicol In vitro, 2003, 17, 279;
[3] Shikishima Y., Takaishi Y., Honda G., Ito M., Takeda Y. Kodzhimatov O. K., Ashurmetov O., Lee K. H.,Chem. Pharm. Bull., 2001, 49(7), 877;
[4] Liu J. H., Planta Medica, 1998, 525;
[5] Honigsmann H., Jaschke E., Gschnait F., Brit. J., Dermatol., 1979, 101(4), 369;
[6] Bates C. G., Saejueng P., Muprhy J. M., VeL Knatarmana D., Org.Lett., 2002,4(26), 4727;
[7] Zheng M. X.,Ge Y. L., Li H. Y., Yan M., Zhou J., Zhang Y., Int. Orthop., 2014, 3(38), 627;
[8] Gia O., Anselmo A., Conconi M.T., Antonello C., Uriarte E., Caffieri S. J., Med.Chem., 1996, 39(22), 4489;
[9] Dalla Via L., Gia O., Magno S. M., Santana L., Teijeira M., Uriaite E. J.,Med. Chem., 1999, 42(21), 4405;
[10] Piscitelli S. C., Burstein A. H., Chaitt D., Alfaro R. M., Falloon J.,Lancet, 2000, 355, 547;
[11] Moore L. B., Goodwin B., Jones S. A., Wisely G. B., Serabjit-Singh C. J., Willson T. M., Collins J. L., Kliewer S. A., Proc. Natl. Acad. Sci. USA, 2000,97, 7500;
[12] Sahi J., Milad M. A., Zheng X. X., Rose K. A., Wang H. B., Stilgenbauer L., Gilbert D., Jolley S., Stern R. H., Lecluyse E., L. J. Pharmacol.Exp. Ther., 2003, 306, 1027;
[13] Howell W. N., Robertson R., J. Chem. Soc., 1937, 293;
[14] Goupil J.-J., Methoxy-psoralen as New Medcament and Process for the Synthesis Thereof,US540586A, 1995 ;
[15] Oda K., Nishizono N., Tamai Y., Yamaguchi Y., Yoshimura T., Wada K., Machida M. J., Heterocycl. Chem., 2005, 65(8), 1985;
[16] Roux D., Maki S., Bevalot F., Humnert P., Syn. Lett., 2007, 1, 129;
[17] Qian H., Liu D. B., Wang L., Chin., J. Appl. Chem., 2009, 26(9), 1084;
[18] Touchstone J. C., Ashmore J., Hulfman M. N., J. Am. Chem. Soc., 1956, 78, 5643;
[19] Hofmann J., Fayez S., Scheiner M., Hoffmann M., Oerter, Chem-Eur J., 2020,26(32), 7299;
[20] Bursavich M. G., Zhang N., Ayral-Kaloustain S., Anderson J. T., Nguyen T. H., Lombardi S., Malwitz D., Brooijmans N., Cole D. C, Gilbert A. M., Nowak P. W., Das S., Tsou H.-R., Venkatesan A. M., Otteng M. A., Harold Birnberg G., MacEwan G. J., 3-Substituted-1H-Infole Compounds, Their Use as Mtor Kinase and PI3 Kinase Inhibitors, and their Syntheses,US20090311217, 2009 ;
[21] Zhang J.-N., Tian B., Jin Z.-M., Liu J.-L., Liu J.-L., Method of Preparing Coumarin Intermediate 4-Methoxy-6-hydroxybenzodihydrofuran,CN201710673357.X, 2017 ;
[22] Danheiser R. M., Heterocycles, 1995, (Sup. I), 573;
[23] Joho E., Israelstam S.,J. Org.Chem., 1960, 26, 240;
[24] Li W. S., Guo Z. R., Thornton J., Wong M., Tetrahedron Lett., 2002, 43, 1923

A New Approach to the Synthesis of Bergapten

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	HUANG Hui-li, LIN Wen-luan, LIN Jian-ming. Chitosan Obtained from Cell Wall of Aspergillus Niger Mycelium [J]. Chemical Research in Chinese Universities, 2004, 20(2): 156-158.
[2]	Chen Zikang, Zhang Yuejun. A Quantitative Study of Solvent Effects on Keto-Enol Tautomeric Equilibria [J]. Chemical Research in Chinese Universities, 1990, 6(1): 76-79.