T3P®-Assisted cascade synthesis of N-acyl α-cyanoamines, cyanoaryl amides and N-acyl cyanoarylamines: Application in making three pharmaceutically important molecules

Akhtar, 2022, Recent trends in the chemistry of Sandmeyer reaction: a review, Mol. Divers., 26, 1837, 10.1007/s11030-021-10295-3 Ayothiraman, 2019, T3P-mediated N–N cyclization for the synthesis of 1,2,4-triazolo[1,5-a]pyridines, Org. Process Res. Dev., 23, 2510, 10.1021/acs.oprd.9b00396 Balakrishna, 2019, T3P® mediated domino C(sp2)–H sulfenylation/annulation of enaminones and methylsulfinyls for the synthesis of chromone thioether derivatives, New J. Chem., 43, 2458, 10.1039/C8NJ05554H Basavaprabhu, 2013, Propanephosphonic acid anhydride (T3P®) - a benign reagent for diverse applications inclusive of large-scale synthesis, Synthesis, 45, 1569, 10.1055/s-0033-1338989 Berger, 2018, A comparative study of the binding properties, dipeptidyl peptidase-4 (DPP-4) inhibitory activity and glucose-lowering efficacy of the DPP-4 inhibitors alogliptin, linagliptin, saxagliptin, sitagliptin and vildagliptin in mice, Endocrinol. Diab. Metab., 1, 10.1002/edm2.2 Biesen, 2021, Multicomponent and one-pot syntheses of quinoxalines, Adv. Synth. Catal., 363, 980, 10.1002/adsc.202001219 Cao, 2023, Palladium- and nickel-catalyzed cascade enantioselective ring-opening/coupling reactions of cyclobutanones, Chem. Commun., 59, 3373, 10.1039/D3CC00205E Castaldi, 2017, A concise and efficient synthesis of vildagliptin, Tetrahedron Lett., 58, 3426, 10.1016/j.tetlet.2017.07.062 Chauhan, 2022, A solid acid catalysed one-pot selective approach for 2,5-diformylfuran synthesis from fructose/carbohydrate feedstocks, Green Chem., 24, 6125, 10.1039/D2GC01728H Chen, 2020, Acyl cyanides as bifunctional reagent: application in copper-catalyzed cyanoamidation and cyanoesterification reaction, J. Org. Chem., 85, 5691, 10.1021/acs.joc.9b03500 Cheng, 2022, Palladium-catalyzed carbene migratory insertion/carbonylation cascade reaction: synthesis of 2-indolones with a C3 all-carbon quaternary center, Org. Lett., 24, 1237, 10.1021/acs.orglett.2c00073 Ciulla, 2019, Cascade reaction based synthetic strategies targeting biologically intriguing indole polycycles, Org. Biomol. Chem., 17, 413, 10.1039/C8OB02620C Cui, 2017, Cascade catalysis via dehydration and oxidation: one-pot synthesis of 2,5-diformylfuran from fructose using acid and V2O5/ceramic catalysts, RSC Adv., 7, 7560, 10.1039/C6RA27678D Das, 2007, An efficient and convenient protocol for the synthesis of quinoxalines and dihydropyrazines via cyclization–oxidation processes using HClO4·SiO2 as a heterogeneous recyclable catalyst, Tetrahedron Lett., 48, 5371, 10.1016/j.tetlet.2007.06.036 Fleming, 2003, Unsaturated nitriles: conjugate additions of carbon nucleophiles to a recalcitrant class of acceptors, Chem. Rev., 103, 2035, 10.1021/cr020045d Fleming, 2010, Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore, J. Med. Chem., 53, 7902, 10.1021/jm100762r Golightly, 2012, Comparative clinical pharmacokinetics of dipeptidyl peptidase-4 inhibitors, Clin. Pharmacokinet., 51, 501, 10.1007/BF03261927 Gonçalves, 2021, Strecker-derived methodology for library synthesis of N-acylated α-aminonitriles, ACS Omega, 6, 1328, 10.1021/acsomega.0c04908 Hazra, 2022, Water: an underestimated solvent for amide bond-forming reactions, ACS Sustainable Chem. Eng., 10, 5299, 10.1021/acssuschemeng.2c00520 Kennedy, 2011, Development of amidine-based sphingosine kinase 1 nanomolar inhibitors and reduction of sphingosine 1-phosphate in human leukemia cells, J. Med. Chem., 54, 3524, 10.1021/jm2001053 Kincaid, 2022, A sustainable synthesis of the SARS-CoV-2 Mpro inhibitor nirmatrelvir, the active ingredient in Paxlovid, Commun. Chem., 5, 156, 10.1038/s42004-022-00758-5 Larock, 1989 Lakshmidevi, 2022, A rapid-room temperature synthesis of α-cyanoacrylates, α-cyanoacrylonitriles and 4H-pyrans using water extract of pomegranate ash as catalytic media, Sustain. Chem. Pharm., 25 Lakshmidevi, 2021, Pd(5%)-KIT-6, Pd(5%)-SBA-15 and Pd(5%)-SBA-16 catalysts in water extract of pomegranate ash: a case study in heterogenization of Suzuki-Miyaura reaction under external base and ligand free conditions, Sustain. Chem. Pharm., 19 Liu, 2010, Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines, Org. Biomol. Chem., 8, 4063, 10.1039/c0ob00223b Mattellone, 2023, Speeding up sustainable solution-phase peptide synthesis using T3P® as a green coupling reagent: methods and challenges, Green Chem., 25, 2563, 10.1039/D3GC00431G Merk, 2014, Extending the structure–activity relationship of anthranilic acid derivatives as farnesoid X receptor modulators: development of a highly potent partial farnesoid X receptor agonist, J. Med. Chem., 57, 8035, 10.1021/jm500937v Morales-Salazar, 2023, Synthesis of bis-furyl-pyrrolo[3,4-b]pyridin-5-ones via Ugi–Zhu reaction and in vitro activity assays against human SARS-CoV-2 and in silico studies on its main proteins, RSC Med. Chem., 14, 154, 10.1039/D2MD00350C Naidu, 2023, Highly economic and waste valorization strategy for multicomponent and Knoevenagel reactions using water extract of tamarind seed ash, Environ. Sci. Pollut. Res., 30, 71420, 10.1007/s11356-022-20124-1 Naidu, 2023, Catalyst-free mechanochemistry as a versatile tool in synthetic chemistry: a review, Green Chem., 25, 6120, 10.1039/D3GC01229H Naidu, 2022, WEPA: a reusable waste biomass-derived catalyst for external oxidant/metal-free quinoxaline synthesis via tandem condensation–cyclization–oxidation of α-hydroxy ketones, Green Chem., 24, 6215, 10.1039/D2GC02386E Nicolaou, 2009, The art of total synthesis through cascade reactions, Chem. Soc. Rev., 38, 2993, 10.1039/b903290h Owen, 2021, An oral SARS-CoV-2 Mpro inhibitor clinical candidate for the treatment of COVID-19, Science, 374, 1586, 10.1126/science.abl4784 Panarese, 2022 Paul, 2016, Synthesis of fused dibenzofuran derivatives via palladium-catalyzed domino C–C bond formation and iron-catalyzed cycloisomerization/aromatization, J. Org. Chem., 81, 1164, 10.1021/acs.joc.5b02637 Pothu, 2022, Recent advances in biomass-derived platform chemicals to valeric acid synthesis, New J. Chem., 46, 5907, 10.1039/D1NJ05777D Procopiou, 2007, 4-Acyl-1-(4-aminoalkoxyphenyl)-2-ketopiperazines as a novel class of non-brain-penetrant histamine H3 receptor antagonists, J. Med. Chem., 50, 6706, 10.1021/jm0708228 Ramirez, 2019, Decarboxylative cyanation of aliphatic carboxylic acids via visible-light flavin photocatalysis, Org. Lett., 21, 1368, 10.1021/acs.orglett.9b00064 Rosenmund, 1919, Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten. I. Mitteilung: ersatz des Halogens durch die Carboxylgruppe, Ber. Dtsch. Chem. Ges. B, 52, 1749, 10.1002/cber.19190520840 Sandmeyer, 1884, Ueber die Ersetzung der Amidgruppe durch Chlor in den aromatischen Substanzen, Ber. Dtsch. Chem. Ges., 17, 1633, 10.1002/cber.18840170219 Schober, 2022, Combination of asymmetric organo- and biocatalysis in flow processes and comparison with their analogous batch Syntheses, Eur. J. Org. Chem., 2022, 10.1002/ejoc.202101035 Sruthi, 2020, An overview of synthetic modification of nitrile group in polymers and applications, J. Polym. Sci., 2020, 1039, 10.1002/pol.20190190 Tomishige, 2022, Hydrodeoxygenation of potential platform chemicals derived from biomass to fuels and chemicals, Green Chem., 24, 5652, 10.1039/D2GC01289H Wang, 2016, BODIPY catalyzed amide synthesis promoted by BHT and air under visible light, Org. Biomol. Chem., 14, 7028, 10.1039/C6OB00736H Wannaporan, 2005, Polymer-supported and polymeric chiral guanidines: preparation and application to the asymmetric Michael reaction of iminoacetate with methyl vinyl ketone, Mol. Divers., 9, 321, 10.1007/s11030-005-8116-z Xie, 2023, Gold-catalyzed cascade reaction of 2-alkynyl aryl azides with enecarbamates for direct synthesis of α-(3-indolyl)ketones, Org. Lett., 25, 421, 10.1021/acs.orglett.2c04147 Yan, 2023, Zeolite catalysts for the valorization of biomass into platform compounds and biochemicals/biofuels: a review, Renew. Sustain. Energy Rev., 178, 10.1016/j.rser.2023.113219 Yashwantrao, 2021, Recent advances in the synthesis and reactivity of quinoxaline, Org. Chem. Front., 8, 2820, 10.1039/D0QO01575J Zhang, 2022, Polymeric organophosphate-hafnium unconventional MOFs nanohybrids enable high-efficiency upgrading of biomass feedstocks via cascade catalytic transfer hydrogenation-dehydration, Ind. Crops Prod., 188, 10.1016/j.indcrop.2022.115606 Zhang, 2018, A dual-functional catalyst for cascade Meerwein–Pondorf–Verley reduction and dehydration of 4′-methoxypropiophenone to anethole, ChemSusChem, 11, 3007, 10.1002/cssc.201801340 Zhang, 2021, Hydrophobicity and co-solvent effects on Meerwein-Ponndorf-Verley reduction/dehydration cascade reactions over Zr-zeolite catalysts, J. Catal., 400, 50, 10.1016/j.jcat.2021.05.011 Zhang, 2023, Ligand-promoted Rosenmund–von Braun reaction, Synlett, 34, 1395, 10.1055/s-0042-1751414