Abstract
Here we demonstrated a solvent free, mechanochemical I2 catalyzed C(sp2)–H sulfenylation of enaminones under grinding condition. Only catalytic amount of I2 is required on silica surface without any external heating. The reaction time has reduced to a great extent in comparison to their solution based counterpart. The frictional energy created by ball-mill on mesoporous silica materials has attracted much attention towards this mechanochemical approach for molecular heterogeneous catalysis. Their large surface area and well defined porous architecture certainly increase the catalytic ability of iodine in this developed protocol. Anti-microbial activities of our synthesized compounds were investigated against two gram positive (Staphylococcus aureus and Bacillus cereus) and two gram negative (Escherichia coli and Klebsiella pneumonia) bacteria. To understand the potency of these compounds (3a–3m) as antimalarial agents, molecular docking studies were also performed. Density functional theory was also used to investigate the chemical reactivity and kinetic stability of the compound 3a–3m.
Similar content being viewed by others
References
Lea MC (1893) On endothermic reactions effected by mechanical force. Am J Sci 46:241–244
Takacs L, Carey ML (2003) The father of mechanochemistry. Bull Hist Chem 1:26–34
Takacs L (2013) The historical development of mechanochemistry. Chem Soc Rev 42:7649–7659
Cheng H, Hernandez JC (2017) Mechanochemical ruthenium-catalyzed hydroarylations of alkynes under ball-milling conditions. Org Lett 19:6284–6287
Haley RA, Zellner AR, Krause JA, Guon H, Mack J (2016) Nickel catalysis in a high speed ball mill: a recyclable mechanochemical method for producing substituted cyclooctatetraene compounds. ACS Sustain Chem Eng 4:2464–2469
James SL, Adams CJ, Bolm C, Braga D, Collier P, Friscic T, Grepioni F, Harris KDM, Hyett G, Jones W, Krebs A, Mack J, Maini L, Orpen AG, Parkin IP, Shearouse WC, Steed JW, Waddell DC (2012) Mechanochemistry: opportunities for new and cleaner synthesis. Chem Soc Rev 41:413–447
Wang G (2013) Mechanochemical organic synthesis. Chem Soc Rev 42:7668–7700
Burmeister CF, Stolle A, Schmidt R, Jacob K, Breitung-Faes S, Kwade A (2014) Experimental and computational investigation of knoevenagel condensation in planetary ball mills. Chem Eng Technol 37:857–864
Schmidt R, Burmeister CF, Balaz M, KwadeA SA (2015) Effect of reaction parameters on the synthesis of 5-arylidene barbituric acid derivatives in ball mills. Org Process Res Dev 19:427–436
Piras CC, Prieto SF, Borggraeve WMD (2019) Ball milling: a green technology for the preparation and functionalisation of nanocellulose derivatives. Nanoscale Adv 1:937–947
Moselage M, Li J, Ackermann L (2016) Cobalt-catalyzed C-H activation. ACS Catal 6:498
Della Ca N, Fontana M, Motti E, Catellani M (2016) Pd/Norbornene: a winning combination for selective aromatic functionalization via C-H bond activation. Acc Chem Res 49:1389
Zhu RY, Farmer ME, Chen YQ, Yu JQ (2016) A simple and versatile amide directing group for C−H functionalizations. Angew Chem Int Ed 55:10578
Drapeau MP, Gooßen LJ (2016) Carboxylic acids as directing groups for C−H bond functionalization. Chem Eur J 22:18654
Yamaguchi J, Muto K, Itami K (2016) Nickel-catalyzed aromatic C-H functionalization. Top Curr Chem 55:374
Gao DW, GuQ ZC, You SL (2017) Synthesis of planar chiral ferrocenes via transition-metal-catalyzed direct C-H bond functionalization. Acc Chem Res 50:351
Schmidt R, Fuhrmann S, Wondraczek L, Stolle A (2016) Influence of reactions parameters on the depolymerization of H2SO4- impregnated cellulose in planetary ball mills. Powder Technol 288:123–131
Mocci R, Murgia S, Luca LD, Colacino E, Delogud F, Porcheddu A (2018) Ball-milling and cheap reagents breathe green life into the one hundred-year-old Hofmann reaction. Org Chem Front 5:531–538
Fulmer DA, Shearouse WC, Medonza ST, Mack J (2009) Solvent-free Sonogashira coupling reaction via high speed ball milling. Green Chem 11:1821–1825
Schneider F, Stolle A, Ondruschka B, Hopf H (2009) The Suzuki-Miyaura reaction under mechanochemical conditions. Org Process Res Dev 13:44–48
Schneider F, Ondruschka B (2008) Mechanochemical solid-state Suzuki reactions using an in situ generated base. Chemsuschem 1:622–625
Waddell DC, Clark TD, Mack J (2012) Conducting moisture sensitive reactions under mechanochemical conditions. Tetrahedron Lett 53:4510–4513
Wang GW, Dong YW, Wu P, Yuan TT, Shen YB (2008) Unexpected solvent-free cycloadditions of 1,3-cyclohexanediones to 1-(Pyridin-2-yl)-enones mediated by manganese(III) acetate in a ball mill. J Org Chem 73:7089
Abedinifar F, Bahadorikhalili S, Larijani B, Mahdavi M, Verpoort F (2022) A review on the latest progress of C-S cross-coupling in diaryl sulfide synthesis: update from 2012 to 2021. Appl Organomet Chem 36:e6482
Wang M, Jiang X (2018) Sulfur-Sulfur bond construction. Top Curr Chem 14:376
Nowrouzi N, Abbasi M, Shahidzadeha ES, Amaleh F (2022) C(sp2)–H bond sulfenylation of aminouracils and enaminones from aryl halides. New J Chem 46:10055–10061
Zhang R, Ding H, Pu X, Qian Z, Xiao Y (2020) Recent advances in the synthesis of sulfides, sulfoxides and sulfones via C-S bond construction from non-halide substrates. Catalysts 10:1339
Rostami A, Rostami A, Ghaderi A (2015) Copper-catalyzed thioetherification reaction of alkyl halides, triphenyltin chloride and arylboronic acids with nitroarenes in the presence of sulfur sources. J Org Chem 80:8694–8704
Naresh G, Kant R, Narender T (2014) Molecular iodine promoted divergent synthesis of benzimidazoles, benzothiazoles, and 2-benzyl-3-phenyl-3,4- dihydro-2H-benzo[e][1,2,4]thiadiazines. J Org Chem 79:3821–3829
Siddaraju Y, Prabhu KR (2016) Iodine-catalyzed cross dehydrogenative coupling reaction: a regioselective sulfenylation of imidazoheterocycles using dimethyl sulfoxide as an oxidant. J Org Chem 81:7838–7846
Ahmed AAR, Waheed EJ, Numan AT (2020) Synthesis, characterization, antibacterial study and efficiency of inhibition of new di-β-enaminone ligand and its complexes. J Phys Conf Ser 1660:012109
Mahmud T, Rehman R, Gulzar A, Khalid A, Anwar J, Shafique U, Waheed-uz-Zaman SM (2010) Synthesis, characterization and study of antibacterial activity of enaminone complexes of zinc and iron. Arab J Chem 3:219–224
Frisch MJT, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JAJ, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar S, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision E.01. Gaussian Inc., Wallingford CT
Sapariyaa NH, Vaghasiyaa BK, Thummara RP, Kamania RD, Patela KH, Thakorb P, Thakkarc SS, Rayc A, Raval DK (2017) Synthesis, characterization, in silico molecular docking study and biological evaluation of 5-(phenylthio) pyrazole based polyhydroquinoline core moiety. New J Chem 41:10686–10694
StephensPJ DFJ, Chabalowski CF et al (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98:11623–11627
Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785
Morris GM, Huey R, Lindstrom W et al (2009) AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 30:2785–2791
Arjunan V, Devi L, Subbalakshmi R et al (2014) Synthesis, vibrational, NMR, quantum chemical and structure-activity relation studies of 2-hydroxy-4-methoxyacetophenone. Spectrochim Acta Part A Mol Biomol Spectrosc 130:164–177
El-Gammal O, Rakha T, Metwally H et al (2014) Synthesis, characterization, DFT and biological studies of isatinpicolinohydrazone and its Zn (II), Cd (II) and Hg (II) complexes. Spectrochim Acta Part A 127:144–156
Verma P, Kuwahara Y, Mori K, Raja R, Yamashita H (2020) Functionalized mesoporous SBA-15 silica: recent trends and catalytic applications. Nanoscale 12:11333–11363
Shen C, Zhang P, Sun Q, Bai S, Hor TSA, Liu X (2015) Recent advances in C-S bond formation via C–H bond functionalization and decarboxylation. Chem Soc Rev 44:291–314
Author information
Authors and Affiliations
Contributions
AI done the experimental work.KS done he computational calculations. AI and PC wrote the main manuscript text. All authors reviewed the manuscript., MB measured the bioactivity of the molecules, PG and RKD edited the manuscript.
Corresponding author
Ethics declarations
Competing interests
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Islam, A., Choudhury, P., Sarkar, K. et al. Molecular iodine catalyzed C(sp2)–H sulfenylation of biologically active enaminone compounds under mechanochemical conditions and studies on their biocidal activity including molecular docking and DFT. Mol Divers (2023). https://doi.org/10.1007/s11030-023-10677-9
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11030-023-10677-9