I2/DMSO-Promoted Synthesis of Chromeno[4,3-b]quinolines through an Imine Formation/Aza-Diels–Alder/Aromatization Tandem Reaction under Metal-Catalyst- and Photosensitizer-Free Conditions

Angélica Peñaranda Gómez; Carlos E. Puerto Galvis; Mario A. Macías; Cristian Ochoa-Puentes; Vladimir V. Kouznetsov

doi:10.1055/a-1638-5030

Synthesis, Table of Contents

Synthesis 2022; 54(07): 1857-1869
DOI: 10.1055/a-1638-5030

paper

I₂/DMSO-Promoted Synthesis of Chromeno[4,3-b]quinolines through an Imine Formation/Aza-Diels–Alder/Aromatization Tandem Reaction under Metal-Catalyst- and Photosensitizer-Free Conditions

Angélica Peñaranda Gómez

^aLaboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia

,

Carlos E. Puerto Galvis

^aLaboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia

,

Mario A. Macías

^bCrystallography and Chemistry of Materials, CrisQuimMat, Department of Chemistry, Universidad de los Andes, Carrera 1 No. 18A 10, Bogotá 111711, Colombia

,

Cristian Ochoa-Puentes

^cLaboratorio de Síntesis Orgánica Sostenible, Departamento de Química, Universidad Nacional de Colombia–Sede Bogotá, Carrera 45 No. 26-85, A.A. 5997, Bogotá, Colombia

,

Vladimir V. Kouznetsov ∗

^aLaboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia

› Author Affiliations

Abstract

All articles of this category

Abstract

A tandem approach was developed for the efficient synthesis of substituted chromeno[4,3-b]quinolines from arylamines and O-cinnamyl salicylaldehydes under metal-catalyst- and photosensitizer-free reaction conditions. Our protocol is based on an inexpensive I₂/DMSO system in which molecular iodine first acts as a Lewis acid to promote the formation of the corresponding imine bearing the alkene moiety; then, this species fulfills a second role by catalyzing an intramolecular aza-Diels–Alder cycloaddition to generate the respective tetrahydrochromenoquinoline as an intermediate. Finally, the dual behavior of DMSO as an oxidant and as a solvent proved crucial at this stage, allowing the regeneration of I₂ and promoting the aromatization of the tetrahydrochromenoquinoline intermediates to yield the desired 7-aryl-6H-chromeno[4,3-b]quinolines. This protocol is mild and easy to perform, features high step-economy (tandem process) and provides a new access to biologically important nitrogen- and oxygen-containing heterocyclic molecules.

Key words

chromeno[4,3-b]quinolines - imines - iodine - tandem reaction - aza-Diels–Alder reaction - oxidation

Full Text

References

References
1 Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. Molecules 2020; 25: 1909
2 Zhi L, Tegley C, Pio B, Edwards J, Motamedi M, Jones T, Marschke K, Mais D, Risek B, Schrader W. J. Med. Chem. 2003; 46: 4104
3 Vu AT, Campbell AN, Harris HA, Unwalla RJ, Manas ES, Mewshaw RE. Bioorg. Med. Chem. Lett. 2007; 17: 4053
4 Kumar AS, Kumar RA, Satyanarayana V, Reddy EP, Reddy BJ. M, Kumar DN, Khuranad A, Chandraiah G, Yadav JS. Nat. Prod. Commun. 2017; 12: 1129
5 Anand Kumar A, Kulbhushan R, Mahendra K. Lett. Drug Des. Discovery 2014; 11: 594
6 Hegab MI, Abdel-Fattah A.-SM, Yousef NM, Nour HF, Mostafa AM, Ellithey M. Arch. Pharm. Chem. Life Sci. 2007; 340: 396
7 Kand D, Kalle AM, Varma SJ, Talukdar P. Chem. Commun. 2012; 48: 2722
8 Kand D, Kalle AM, Talukdar P. Org. Biomol. Chem. 2013; 11: 1691
9 Huang W, Lin W, Guan X. Tetrahedron Lett. 2014; 55: 116
10 Jones W, Kiselyov AS. Tetrahedron Lett. 2000; 41: 2309

11a Nagarajan R, Ramesh S, Gaddam V. Synlett 2010; 757
11b Sharghi H, Khalifeh R, Rashidi Z. Mol. Diversity 2013; 17: 721
11c Rahimzadeh G, Soheilizad M, Kianmehr E, Larijani B, Mahdavic M. ARKIVOC 2018; (v): 20

12 Yu X, Wang J, Xu Z, Yamamoto Y, Bao M. Org. Lett. 2016; 18: 2491
13 Aradi K, Bombicz P, Novak Z. J. Org. Chem. 2016; 81: 920
14 Shiri M, Fathollahi-Lahroud M, Yasaei Z. Tetrahedron 2017; 73: 2501
15 Dong W, Yuan Y, Gao X, Hu B, Xie X, Zhang Z. ChemCatChem 2018; 10: 2878

16a Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
16b Plesniak MP, Huang H.-M, Procter DJ. Nat. Rev. Chem. 2017; 1: 0077

17 Behr A, Vorholt AJ, Ostrowski KA, Seidensticker T. Green Chem. 2014; 16: 982

18a Echeverry-Gonzalez CA, Puerto Galvis CE, Borca CH, Mosquera MA, Luis-Robles AF, Kouznetsov VV. Org. Chem. Front. 2019; 6: 3374
18b Peñaranda Gómez A, Rodríguez Bejarano O, Kouznetsov VV, Ochoa-Puentes C. ACS Sustainable Chem. Eng. 2019; 7: 18630
18c Orozco D, Kouznetsov VV, Bermúdez A, Vargas Méndez LY, Mendoza Salgado AR, Meléndez Gómez CM. RSC Adv. 2020; 10: 4876

19a Jia X, Peng F, Qing C, Huo C, Wang X. Org. Lett. 2012; 14: 4030
19b Jia X, Wang Y, Peng F, Huo C, Yu L, Liu J, Wang X. J. Org. Chem. 2013; 78: 9450
19c Wang Y, Peng F, Liu J, Huo C, Wang X, Jia X. J. Org. Chem. 2015; 80: 609

20 Liu J, Liu F, Zhu Y, Ma X, Jia X. Org. Lett. 2015; 17: 1409
21 Mandal S, Bera T, Dubey G, Saha J, Laha JK. ACS Catal. 2018; 8: 5085

22a Reddy PN, Subba Reddy BV, Padmaja P. Curr. Org. Synth. 2018; 15: 815
22b Monga A, Bagchi S, Sharma A. New J. Chem. 2018; 42: 1551

23a Wu Y.-D, Geng X, Gao Q, Zhang J, Wu X, Wu A.-X. Org. Chem. Front. 2016; 3: 1430
23b Yi X, Jiao L, Xi C. Org. Biomol. Chem. 2016; 14: 9912

24 Tashrifi Z, Khanaposhtani MM, Larijani B, Mahdavi M. Adv. Synth. Catal. 2020; 362: 65
25 Kouznetsov VV. Tetrahedron 2009; 65: 2721
26 Le ST, Yasuoka C, Asahara H, Nishiwaki N. Molecules 2016; 21: 827
27 Mohammed S, Vishwakarma RA, Bharate SB. J. Org. Chem. 2015; 80: 6915
28 Rafique J, Saba S, Rosrio AR, Braga AL. Chem. Eur. J. 2016; 22: 11854

29a Li X, Mao Z, Wang Y, Chen W, Lin X. Tetrahedron 2011; 67: 3858
29b Gao Q, Liu S, Wu X, Zhang J, Wu A. J. Org. Chem. 2015; 80: 5984
29c Jin G, Zhao J, Han J, Zhu S, Zhang J. Tetrahedron 2010; 66: 913

30 Zhou P, Pan Y, Tan H, Liu W. J. Org. Chem. 2019; 84: 1566
31 CrysAlis^Pro 1.171.39.46e; Rigaku Oxford Diffraction, 2018.
32 CCDC 2055070 (8a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
33 Twin H, Batey RA. Org. Lett. 2004; 6: 4913

Supplementary Material

Supporting Information