Abstract
A new ONO-tridentate Schiff base ligand (H2L) derived from 3-methoxysalicylaldehyde and nicotinic hydrazide was synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, UV–Vis, and powder XRD studies. Then, oxovanadium(V) and dioxomolybdenum(VI) Schiff base complexes, VOL and MoO2L, were also prepared and characterized by different techniques. Moreover, the catalytic activities of both complexes were investigated for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles under reflux conditions as well as through ultrasonic irradiation. The results revealed several advantages of this procedure, including high product yields, short reaction times, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, and green aspects by avoiding toxic catalysts and solvents.
Graphic abstract
Similar content being viewed by others
References
Kebede E, Tadikonda R, Nakka M, Inkollu B, Vidavalur S (2015) Eur J Org Chem https://doi.org/10.1002/ejoc.201500803
Alaqeel SI (2017) J Saudi Chem Soc 21:229
Di Gioia ML, Cassano R, Costanzo P, Herrera Cano N, Maiuolo L, Nardi M, Nicoletta FP, Oliverio M, Procopio A (2019) Molecules 24:2885
Yadav G, Ganguly S (2015) Eur J Med Chem 97:419
Algul O, Karabulut A, Canacankatan N, Gorur A, Sucu N, Vezir O (2012) Med Chem 11:267
Sharghi H, Asemani O, Tabaei SMH (2008) J Heterocycl Chem 45:1293
Stuchlikova L, Jirasko R, Skalova L, Pavlik F, Szotakova B, Holcapek M, Vanek T, Podlipna R (2016) Chemosphere 157:10
Ranjan N, Kumar S, Watkins D, Wang D, Appela DH, Arya DP (2013) Bioorg Med Chem Lett 23:5689
Roth T, Morningstar ML, Boyer PL, Hughes SH, Buckheit RW, Michejda CJ (1997) J Med Chem 40:4199
Chi Y-C, Sun CM (2000) Synlett 5:591–594
Dudd LM, Venardou E, Garcia-Verdugo E, Licence P, Blake AJ, Wilson C, Poliakoff M (2003) Green Chem 5:187
Bahrami K, Khodaei MM, Kavianima I (2007) Synthesis 417
Sharghi N, Asemani O, Khalifeh R (2008) Synth Commun 38:1128
Narang U, Yadav KK, Bhattacharya S, Chauhan SM (2017) ChemistrySelect 2:7135
Nguyen TT, Nguyen XT, Nguyen TL (2019) ACS Omega 4:368
Perston PN (1981) The Chemistry of Heterocyclic Compounds, Benzimidazoles and Congeneric Tricyclic Compounds, Part 1. Wiley, New York, 40:6
Grimmett MR (1984) Imidazoles and their benzo derivatives. In: Katritzky AR, Rees CW (eds) Comprehensive Heterocyclic Chemistry, vol 5. Pergamon Press, Oxford, p 457
Gadekar SL, Arbad RB, Machhindra KL (2010) Chin Chem Lett 21:1053
Cano NH, Uranga JG, Nardi M, Procopio A, Wunderlin DA, Santiago AN (2016) Beilstein J Org Chem 12:2410
Khan AT, Parvin T, Choudhury LH (2009) Synth Commun 39:2339
Rezaee Nezhad E, Tahmasebi R (2019) Asian J Green Chem 3:34
Alinezhad H, Salehian F, Biparva P (2012) Synth Commun 42:102
Nale DB, Bhanage B (2015) Synlett 2835
Chari MA, Shobha D, Kenawy E, Al-Deyab SS, Reddy BVS, Vinu A (2010) Tetrahedron Lett 51:5195
Hanoon HD, Kowsari E, Abdouss M, Zandi H, Ghasemi MH (2017) Res Chem Intermed 43:1751
Kaur N, Kaur S, Kaur G, Bhalla A, Srinivasan S, Chaudhary GR (2019) J Mater Chem A 7:17306
Haghighat M, Golshekan M, Shirini F (2019) ChemistrySelect 4:7968
Bahrami K, Bakhtiarian M (2018) ChemistrySelect 3:10875
Kelkar MA, Gogate RP, Pandit AB (2006) Ultrason Sonochem 13:523
Margulis MA (1995) Sonochemistry and Cavitation. Australia ; [Langhorne, Pa., U.S.] : Gordon and Breach Publishers
Moghadam M, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I, Kargar H (2009) J Iran Chem Soc 6:251
Mahamuni NN, Gogate RP, Pandit AB (2007) Ultrason Sonochem 14:135
Heidari F, Fatemi SJA, Ebrahimipour SY, Ebrahimnejad H, Castro J, Dusek M, Eigner V (2017) Inorg Chem Commun 76:1
Quintal S, PiresdaSilva MJ, Martins SRM, Sales R, Felix V, Drew MGB, Meirels M, Mourato AC, Nunes CD, Saraiva MS, Machuqueiro M, Calhorda MJ (2019) Dalton Trans 48:8449
Pisk J, Bilić L, Đaković M, Cvijanović D, Damjanović V, Lovrić J, Rubčić M, Vrdoljak V, Cindrić M (2018) Polyhedron 145:70
Nag P, Bohra R, Mehrotra RC (2002) J Chem Res 86
Zhang WG, Liang JH (2017) Russ J Coord Chem 43:411
Hossain MK, Haukka M, Sillanpää R, Hrovat DA, Richmond MG, Nordlander E, Lehtonen A (2017) Dalton Trans 46:7051
Yang Y, Hao S, Zhang Y, Kan Q (2011) Solid State Sci 13:1938
Ta S, Ghosh M, Ghosh K, Brandão P, Félix V, Hira SK, Manna PP, Das D (2019) ACS Appl Bio Mater 2:2802
Wang Q, Xiong ZD, Liu L, Cai YJ (2021) Inorg Nano-Met Chem 51:12
Safaiee M, Moeinimehr M, Zolfigol MA (2019) Polyhedron 170:138
Liang M, Sun N, Zou D-H (2018) Acta Chim Slov 65:964
Xue L-W, Peng Q-L, Wang P-P, Zhang H-J (2019) Acta Chim Slov 66:694
Hatefi M, Moghadam M, Sheikhshoaei I, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I, Kargar H (2009) Appl Catal A Gen 370:66
Moghadam M, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I, Kargar H, Sheikhshoaei I, Hatefi M (2011) J Iran Chem Soc 8:1019
Kargar H (2011) Inorg Chem Commun 14:863
Moshref Javadi M, Moghadam M, Mohammadpoor-Baltork I, Tangestaninejad S, Mirkhani V, Kargar H, Tahir MN (2014) Polyhedron 72:19
Kargar H (2014) Transit Met Chem 39:811
Vrdoljak V, Prugovecki B, Calogovic DM, Pisk J, Dreos R, Siega P (2011) Cryst Growth Des 11:1244
Kia R, Kargar H (2015) J Coord Chem 68:1441
Kurbah SD, Asthana M, Syiemlieh I, Lywait AA, Longchar M, Lal RA (2018) J Organomet Chem 876:10
Li Y, Xu L, Duan M, Wu J, Wang Y, Dong K, Han M, You Z (2019) Inorg Chem Commun 105:212
Gao S, Zhang XF, Huo LH, Zhao H (2004) Acta Crystallogr E60:m1731
Rana A, Dinda R, Sengupta P, Ghosh S, Falvello LR (2002) Polyhedron 21:1023
Mahato S, Meheta N, Kotakonda M, Joshi M, Ghosh P, Shit M, Choudhury AR, Biswas B (2020) Appl Organomet Chem 34:e5935
Mahato S, Meheta N, Kotakonda M, Joshi M, Shit M, Choudhury AR, Biswas B (2020) Polyhedron 194:114933
Mudi PK, Bandopadhyay N, Joshi M, Shit M, Paul S, Choudhury AR, Biswas B (2020) Inorg Chim Acta 505:119468
Pal CK, Mahato S, Joshi M, Paul S, Choudhury AR, Biswas B (2020) Inorg Chim Acta 506:119541
Sen SK, Al Mortuza A, Manir MS, Pervez MF, Hossain SMAI, Alam MS, Haque MAS, Matin MA, Hakim MA, Huda A (2020) Nano Ex 1:020026
Fallah-Mehrjardi M, Ayazi M, Banitaba SH (2020) Iran Chem Commun 8:80
Teimouri A, Chermahini AN, Salavati H, Ghorbanian L (2013) J Mol Catal A Chem 373:38
Kumar KR, Satyanarayana PVV, Reddy BS (2013) J Chem 2013:151273
Digwal CS, Yadav U, Sakla AP, Ramya PVS, Aaghaz S, Kamal A (2016) Tetrahedron Lett 57:4012
Xiangming H, Huiqiang M, Yulu W (2007) ARKIVOC xiii:150
Chari MA, Shobha D, Sasaki T (2011) Tetrahedron Lett 52:5575
Sadeghi B, Ghasemi Nejad M (2013) J Chem 2013:581465
Inamdar SM, More VK, Mandal SK (2013) Tetrahedron Lett 54:579
Azizian J, Torabi P, Noei J (2016) Tetrahedron Lett 57:185
Bharathi M, Indira S, Vinoth G, Mahalakshmi T, Induja E, Bharathi KS (2020) J Coord Chem 73:653
Acknowledgements
We gratefully acknowledge the practical support of this study by Ardakan University and Payame Noor University.
Author information
Authors and Affiliations
Corresponding author
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
About this article
Cite this article
Kargar, H., Kargar, K., Fallah-Mehrjardi, M. et al. Syntheses, characterization, and catalytic potential of novel vanadium and molybdenum Schiff base complexes for the preparation of benzimidazoles, benzoxazoles, and benzothiazoles under thermal and ultrasonic conditions. Monatsh Chem 152, 593–605 (2021). https://doi.org/10.1007/s00706-021-02780-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-021-02780-0