Efficient Synthesis of Pyrido[3,2-c]coumarins via Silver Nitrate Catalyzed Cycloisomerization and Application to the First Synthesis of Polyneomarline C

Jeong A Yoon; Young Taek Han

doi:10.1055/s-0037-1610730

Synthesis, Table of Contents

Synthesis 2019; 51(24): 4611-4618
DOI: 10.1055/s-0037-1610730

paper

Efficient Synthesis of Pyrido[3,2-c]coumarins via Silver Nitrate Catalyzed Cycloisomerization and Application to the First Synthesis of Polyneomarline C

Jeong A Yoon

,

Young Taek Han∗

College of Pharmacy, Dankook University, Chenan 31119, Korea Email: hanyt@dankook.ac.kr

› Author Affiliations

Abstract

All articles of this category

Abstract

Herein, we report an efficient method for the synthesis of the pyrido[3,2-c]coumarin scaffold, one of the privileged heterocycle-fused coumarin scaffolds, via a AgNO₃-catalyzed cycloisomerization of 4-(propynylamino)coumarins obtained from diverse 4-hydroxycoumarins. This concise method affords pyrido[3,2-c]coumarin analogues bearing diverse substituents on the benzene or pyridine ring in moderate to good yields. Moreover, this methodology was extended to the facile synthesis of polyneomarline C, a natural pyrido[3,2-c]coumarin derivative isolated from the Chinese herbal medicine Polyalthia nemoralis A. DC., in three steps and in 26% overall yield from the known 4-hydroxycoumarin.

Key words

cycloisomerization - pyrido[3,2-c]coumarin - polyneomarline C - heterocycle-fused coumarin - propargylamine

Full Text

References

References

1a Detsi A, Kontogiorgis C, Hadjipavlou-Litina D. Expert Opin. Ther. Pat. 2017; 27: 1201
1b Medina FG, Marrero JG, Macías-Alonso M, González MC, Córdova-Guerrero I, García AG. T, Osegueda-Robles S. Nat. Prod. Rep. 2015; 32: 1472

2 Connor DT, Unangst PC, Schwender CF, Sorenson RJ, Carethers ME, Puchalski C, Brown RE, Finkel MP. J. Med. Chem. 1989; 32: 683
3 Khan IA, Kulkarni MV, Gopal M, Shahabuddin M, Sun C.-M. Bioorg. Med. Chem. Lett. 2005; 15: 3584
4 Raev L, Voinova E, Ivanov I, Popov D. Pharmazie 1990; 45: 696
5 Patel AA, Lad HB, Pandya KR, Patel CV, Brahmbhatt DI. Med. Chem. Res. 2013; 22: 4745
6 Nunez-Vergara LJ, Squella JA, Navarrete-Encina PA, Vicente-García E, Preciado S, Lavilla R. Curr. Med. Chem. 2011; 18: 4761

7a Sakthivel S, Sharma A, Balamurugan R. Eur. J. Org. Chem. 2017; 3941
7b Nizami TA, Hua R. Tetrahedron 2017; 73: 6080
7c Vessally E, Hosseinian A, Edjlali L, Bekhradnia A, Esrafilie MD. RSC Adv. 2016; 6: 71662
7d Saito A, Konishi T, Hanzawa Y. Org. Lett. 2010; 12: 372

8 Ahn S, Yoon JA, Han YT. Synthesis 2019; 51: 552

9a Belal M, Das DK, Khan AT. Synthesis 2015; 47: 1109
9b Khan AT, Das DK, Islam K, Das P. Tetrahedron Lett. 2012; 53: 6418

10a Vishnumurthy K, Makriyannis A. J. Comb. Chem. 2010; 12: 664
10b Tagawa Y, Yamagata K, Sumoto K. Lett. Org. Chem. 2006; 3: 759

11 Tao XZ, Dai JJ, Zhou J, Xu J, Xu HJ. Chem. Eur. J. 2018; 24: 6932
12 Pave G, Chalard P, Viaud-Massuard M.-C, Troin Y, Guillaumet G. Synlett 2003; 7: 987

13a Yadav A, Biswas S, Mobin SM, Samanta S. Tetrahedron Lett. 2017; 58: 3634
13b Ling F, Xiao L, Fang L, Lv Y, Zhong W. Adv. Synth. Catal. 2018; 360: 444
13c Motamedi R. Chem. Heterocycl. Comp. 2013; 48: 1839
13d Kolita S, Bhuyan PJ. ChemistrySelect 2018; 3: 1441

14 Lu Z.-M, Zhang Q.-J, Chen R.-Y, Yu D.-Q. J. Asian Nat. Prod. Res. 2008; 10: 656
15 Pisani L, Muncipinto G, Miscioscia TF, Nicolotti O, Leonetti F, Catto M, Caccia C, Salvati P, Soto-Otero R, Mendez-Alvarez E. J. Med. Chem. 2009; 52: 6685
16 Nishizawa R, Nishiyama T, Hisaichi K, Hirai K, Habashita H, Takaoka Y, Tada H, Sagawa K, Shibayama S, Maeda K. Bioorg. Med. Chem. 2010; 18: 5208
17 Han YT. Tetrahedron Lett. 2017; 58: 556

18a Jiang K.-M, Kang J.-A, Jin Y, Lin J. Org. Chem. Front. 2018; 5: 434
18b Vallerotto S, Le Douaron G, Bernadat G, Ferrié L, Figadère B. Synthesis 2016; 48: 3232
18c Aichhorn S, Himmelsbach M, Schoefberger W. Org. Biomol. Chem. 2015; 13: 9373
18d Cao K, Zhang FM, Tu YQ, Zhuo XT, Fan CA. Chem. Eur. J. 2009; 15: 6332

19a Nolan KA, Doncaster JR, Dunstan MS, Scott KA, Frenkel AD, Siegel D, Ross D, Barnes J, Levy C, Leys D. J. Med. Chem. 2009; 52: 7142
19b Rao ML. N, Kumar A. Tetrahedron 2014; 70: 6995

20 Sonawane AD, Shaikh YB, Garud DR, Koketsu M. Synthesis 2019; 51: 500
21 Zhang W, Li Z, Zhou M, Wu F, Hou X, Luo H, Liu H, Han X, Yan G, Ding Z, Li R. Bioorg. Med. Chem. Lett. 2014; 24: 799
22 Huang C.-N, Kuo P.-Y, Lin C.-H, Yang D.-Y. Tetrahedron 2007; 63: 10025

Supplementary Material

Supporting Information