Synthesis, Table of Contents Synthesis 2025; 57(12): 1997-2003DOI: 10.1055/a-2567-4644 paper Ag(I)/Au(I)-Catalyzed Domino Propargylation/Aza-Annulation to Access Coumarino[4,3-b]pyridines Authors Author Affiliations Chada Raji Reddy ∗ a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India Venkatareddy Edhara a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India Ankita Kumari a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India Adla Vijender a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract An approach for the synthesis of diversely substituted coumarino[4,3-b]pyridines (5H-[1]benzopyrano[4,3-b]pyridin-5-ones), involving the annulation of 4-aminocoumarins with propargylic alcohols, is reported. The reaction proceeds through C-3 propargylation followed by an aza-annulation in a domino manner in the presence of AgSbF6/AuCl(PPh3) as the catalytic system. The products can be synthesized from a broad range of propargylic alcohols, demonstrating the compatibility with different functional groups. Key words Key wordscoumarino[4,3-b]pyridine - 5H-[1]benzopyrano[4,3-b]pyridin-5-one - propargylic alcohol - propargylation - aza-annulation - domino reaction Full Text References References For selected references, see 1a Douka MD, Litinas KE. Molecules 2022; 27: 7256 1b Patra P, Kar GK. New J. Chem. 2021; 45: 2879 1c Patra P. ChemistrySelect 2019; 4: 2024 For selected papers, see: 2a Adib M, Peytam F, Jazi MR, Khanaposhtani MM, Mahernia S, Bijanzadeh HR, Jahani M, Imanparast S, Faramarzi MA, Mahdavig M, Larijani B. New J. Chem. 2018; 42: 17268 2b Encinas EM, Rubiales G, Knudssen BR, Palacios F, Alonso C. Eur. J. Med. Chem. 2019; 178: 752 2c Liendo AR, Jiménez IA, Encinas EM, Sifaoui I, Batlle MR, Pellicer JC, Alonso C, Palacios F, Piñero JE, Morales JL. Pharmaceuticals 2021; 14: 1013 2d Gouda MA. S, Salem MA. I, Marzouk MI, Mahmoud NF. H, Ismail MF. Chem. Biodiversity 2023; 20: e202300706 2e Yu J, Gao M, Zhao R, Liu H, Fan H, Pan L, Jin J. Phytochem. Lett. 2023; 57: 5 3 Wang XL, Dou M, Luo Q, Cheng LZ, Yan YM, Li RT, Cheng YX. Fitoterapia 2016; 12: 4 4 Pang M, Lee J, Jeon JH, Song IS, Han YT, Choi MK. Mass Spectrom. Lett. 2021; 12: 200 For representative references, see: 5a Kosuge S, Araki Y, Tsuge K, Sugimoto K, Matsuya Y. J. Org. Chem. 2023; 88: 6973 5b Jourjine IA. P, Bracher F. Eur. J. Org. Chem. 2023; 26: e202300399 5c Patel AK, Samanta S. Eur. J. Org. Chem. 2023; 26: e202300631 For selected references, see: 6a Mulakayala N, Rambabu D, Raja MR, Chaitanya M, Kumar CS, Kalle AM, Krishna GR, Reddy CM, Rao MV. B, Pal M. Bioorg. Med. Chem. 2012; 20: 759 6b Ling F, Xiao L, Fang L, Lv Y, Zhong W. Adv. Synth. Catal. 2018; 360: 444 6c Beccalli EM, Contini A, Trimarco P. Tetrahedron Lett. 2004; 45: 3447 For selected papers, see: 7a Yadav A, Biswas S, Mobin SM, Samanta S. Tetrahedron Lett. 2017; 58: 3634 7b ref 2e. 8a Ataee-Kachouei T, Nasr-Esfahani M, Mohammadpoor-Baltork I, Mirkhani V, Moghadam M, Tangestaninejad S, Notash B. Appl. Organomet. Chem. 2020; 34: e5948 8b Jadhav G, Medhane V, Deshmukh D. Lett. Org. Chem. 2021; 18: 862 9 Yoon JA, Han YT. Synthesis 2019; 51: 4611 For selected references, see: 10a Reddy CR, Nair K, Srinivasu E, Subbarao M, Grée R. J. Org. Chem. 2024; 89: 2675 10b Reddy CR, Aila M, Subbarao M, Warudikar K, Grée R. Org. Lett. 2021; 23: 4882 10c Chada RR, Kajare RC, Bhandari MC, Mohammed SZ, Khatravath M, Warudikara K, Punna N. Org. Biomol. Chem. 2021; 19: 809 10d Reddy CR, Subbarao M, Sathish P, Kolgave DH, Donthiri RR. Org. Lett. 2020; 22: 689 10e Reddy CR, Valleti RR, Sathish P. J. Org. Chem. 2017; 82: 2345 11a Veenboera RM. P, Nolan SP. Green Chem. 2015; 17: 3819 11b Biannic B, Aponick A. Eur. J. Org. Chem. 2011; 6605 11c Halliday CJ. V, Lynam JM. Dalton Trans. 2016; 45: 12611 12 Sharma A, Gogoi P. Org. Biomol. Chem. 2019; 17: 9014 13a Liu P, Deng C.-L, Lei X, Lin G.-q. Eur. J. Org. Chem. 2011; 7308 13b Jeong Y, Kim BI, Lee JK, Ryu JS. J. Org. Chem. 2014; 79: 6444 13c Schömberg F, Zi Y, Vilotijevic I. Chem. Commun. 2018; 54: 3266 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)
