Zinc Oxide Nanoparticles Catalysed One-Pot Three-Component Reaction: A Facile Synthesis…
regioselective “ligation” of azides and terminal alkynes. Angew
4 Conclusion
Chem Int Ed 41:2596–2599
9. Yang Y, Rasmussen BA, Shlaes DM (1999) Class A
β-lactamases—enzyme-inhibitor interactions and resistance.
Pharmacol Ther 83:141–151
Highly stable, pure hexagonal wurtzite structure of ZnO
nanocrystals having plates/sheets type of architecture with
sizes 15‒25 nm have been prepared from Zn(OAc)2·2H2O
precursor in the presence of PEG-400 under ultrasonic irra-
diation. The as-synthesized nanoparticles were well char-
acterized for structural purity and morphology study. The
as-synthesized ZnO nanocrystals catalysed one-pot, three
component reaction described here provides an efcient,
facile and step-economic method for the synthesis of 4-aryl-
NH-1,2,3-triazoles using aldehydes, nitroalkane and sodium
azide in PEG 400 solvent. The reaction condition tolerated
a wide array of electronically diverse substrates and also
employed readily available cheap starting materials, thus
providing a convenient approach for synthesis of these sub-
stituted NH-1,2,3-triazoles.
10. Dhumal ST, Deshmukh A, Kharat KR, Sathe BR, Chavan SS,
Mane RA (2019) Copper fuorapatite assisted synthesis of new 1,
2, 3-triazoles bearing a benzothiazolyl moiety and their antibacte-
rial and anticancer activities. New J Chem 43:7663–7673
11. Ali AA, Gogoi D, Chaliha AK, Buragohain AK, Trivedi P, Saikia
PJ, Gehlot PS, Kumar A, Chaturvedi V, Sarma D (2017) Synthesis
and biological evaluation of novel 1, 2, 3-triazole derivatives as
anti-tubercular agents. Bioorg Med Chem Lett 16:3698–3703
12. Thirumurugan P, Matosiuk D, Jozwiak K (2013) Click chemistry
for drug development and diverse chemical–biology applications.
Chem Rev 113:4905–4979
13. Liu YH, Zhang L, Xu XN, Li ZM, Zhang DW, Zhao X, Li ZT
(2014) Intramolecular C–H···F hydrogen bonding-induced 1, 2,
3-triazole-based foldamers. Org Chem Front 1:494–500
14. Lau YH, Rutledge PJ, Watkinson M, Todd MH (2011) Chemical
sensors that incorporate click-derived triazoles. Chem Soc Rev
40:2848–2866
15. Hanselmann R, Job GE, Johnson G, Lou RL, Martynow JG, Reeve
MM (2010) Synthesis of an antibacterial compound containing a
1, 4-substituted 1 H-1, 2, 3-triazole: A scaleable alternative to the
“click” reaction. Org Process Res Dev 14:152–158
Acknowledgements D.S. is thankful to DST, New Delhi, India for
a research grant [No. EMR/2016/002345]. S.A. is grateful to SERB,
India for research fellowship. K.D. thanks SERB-DST, India (Grant
EEQ/2018/000326) and UGC, India (Grant No.F.30-467/2019-BSR)
for fnancial support. We thank Dibrugarh University for providing all
the infrastructural facility, IIT-Delhi for FESEM and AIIMS, Delhi for
HRTEM facility. The authors acknowledge the Department of Science
and Technology for fnancial assistance under DST-FIST programme
and UGC, New Delhi for Special Assistance Programme (UGC-SAP)
to the Department of Chemistry, Dibrugarh University.
16. Chabre YM, Roy R (2008) Recent trends in glycodendrimer syn-
theses and applications. Curr Top Med Chem 8:1237–1285
17. da Silva FDC, de Souza MCB, Frugulhetti II, Castro HC, Silmara
LDO, de Souza TML, Rodrigues DQ, Souza AM, Abreu PA, Pas-
samani F, Rodrigues CR (2009) Synthesis, HIV-RT inhibitory
activity and SAR of 1-benzyl-1H-1, 2, 3-triazole derivatives of
carbohydrates. Eur J Med Chem 44:373–383
18. Bozorov K, Zhao J, Aisa HA (2019) 1,2,3-Triazole-containing
hybrids as leads in medicinal chemistry: A recent overview.
Bioorg Med Chem 27:3511–3531
Compliance with Ethical Standards
19. Rohrig UF, Awad OL, Grosdidier OA, Larrieu P, Stroobant V,
Colau D, Cerundolo V, Simpson AJG, Vogel P, Van den Eynde
BJ, Zoete V, Michielin O (2010) Rational design of indoleamine
2, 3-dioxygenase inhibitors. J Med Chem 53:1172–1189
20. Panzarasa G (2018) Just Add Luminol to Turn the Spotlight on
Radziszewski Amidation. ACS Omega 3(10):13179–13182
21. Lanigan RM, Starkov P, Sheppard TD (2013) Direct synthesis of
Conflict of interest The authors declare no competing fnancial interest.
References
amides from carboxylic acids and amines using B (OCH
Org Chem 78(9):4512–4523
2CF3)3. J
1. Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA
(1996) Multiple-component condensation strategies for combina-
torial library synthesis. Acc Chem Res 29:123–131
22. Ghose AK, Viswanadhan VN, Wendoloski JJ (1999) J Combin
Chem 1:55–68
2. Laurent A, Gerhardt CF (1838) Ueber einige Stickstofverbindun-
gen des Benzoyls. Ann Chim Phys 66:181–181
23. Carey JS, Lafan D, Thomson C, Williams MT (2006) Org Biomol
Chem 4:2337–2347
3. Kakuchi R, Theato P (2013) Three-component reactions for post-
polymerization modifcations. ACS Macro Lett 2:419–422
4. Pandey G, Singh RP, Garg A, Singh VK (2005) Synthesis of
Mannich type products via a three-component coupling reaction.
Tetrahedron Lett 46:2137–2140
24. Suppo JS, de Figueiredo RM, Campagne JM (2003) Dipeptide
Syntheses via Activated α-Aminoesters. Org Synth 92:296–308
25. Chen Y, Wendt-Pienkowski E, Ju J, Lin S, Rajski SR, Shen B
(2010) Characterization of FdmV as an amide synthetase for fred-
ericamycin A biosynthesis in Streptomyces griseus ATCC 43944.
J Biol Chem 285(50):38853–38860
5. Garg A, Ali AA, Damarla K, Kumar A, Sarma D (2018) Aque-
ous bile salt accelerated cascade synthesis of 1,2,3-triazoles from
arylboronic acids. Tetrahedron lett 59:4031–4035
26. Valverde IE, Mindt TL (2013) 1, 2, 3-Triazoles as amide-bond
surrogates in peptidomimetics. CHIMIA International Journal for
Chemistry 67(4):262–266
6. Ali AA, Konwar M, Chetia M, Sarma D (2016) [Bmim] OH medi-
ated Cu-catalyzed azide–alkyne cycloaddition reaction: a potential
green route to 1,4-disubstituted 1,2,3-triazoles. Tetrahedron Lett
57:5661–5665
27. Weide T, Saldanha SA, Minond D, Spicer TP, Fotsing JR, Spaar-
garen M, Frère JM, Bebrone C, Sharpless KB, Hodder PS, Fokin
VV (2010) NH-1, 2, 3-triazole inhibitors of the VIM-2 metallo-
β-lactamase. ACS Med Chem Lett 1:150–154
7. Tornoe CW, Christensen C, Meldal M (2002) Peptidotriazoles on
solid phase: [1,2,3]-triazoles by regiospecifc copper (I)-catalyzed
1, 3-dipolar cycloadditions of terminal alkynes to azides. J Org
Chem 67:3057–3064
28. Röhrig UF, Majjigapu SR, Grosdidier A, Bron S, Stroobant V,
Pilotte L, Colau D, Vogel P, Van den Eynde BJ, Zoete V, Michielin
O (2012) Rational design of 4-aryl-1, 2, 3-triazoles for indoleam-
ine 2, 3-dioxygenase 1 inhibition. J Med Chem 55:5270–5290
8. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A
stepwise huisgen cycloaddition process: copper (I)-catalyzed
1 3