Synthesis of Amidation Agents and Their Reactivity in Condensation Reactions

Abstract

Nowadays, the development of new approaches which smartly bypass the use of harsh reaction conditions and hazardous chemicals covers a pivotal role. In this research paper the synthesis, characterization, and application of novel libraries of triazine bis-quaternary ammonium salts, employed as coupling agents to produce amides is reported. Full characterization of the novel compounds by ¹H and ¹³C NMR, FT-IR spectroscopy, ESI-HRMS, and elemental analysis is provided. Furthermore, a comparison in terms of activity of the preformed triazine compounds versus in situ formulations has been evaluated for the formation of amides in the presence of phenylethylamine and different aliphatic or aromatic acids. A possible correlation between the chemical structure of the triazine and their reactivity for the formation of the triazine bis-quaternary ammonium salts is also reported. Moreover, best performing condensation agents have been further tested for the cross-linking of collagen powder as possible wet white tanning systems, for sustainable and environmentally friendly leather tanning.

Key words

1,3,5-triazine bis-quaternary ammonium salts - amidation agents - collagen cross-linking - green chemistry - sustainable leather tanning

Publication History

Received: 08 November 2020

Accepted after revision: 10 December 2020

Accepted Manuscript online:
10 December 2020

Article published online:
18 January 2021

• References

• 1a El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
• 1b Lanigan RM, Sheppard TD. Eur. J. Org. Chem. 2013; 7453
• 1c Krause T, Baader S, Erb B, Gooßen LJ. Nat. Commun. 2016; 7: 11732
• 1d Rajput P, Sharma A. J. Pharmacol. Med. Chem. 2018; 2: 22 https://www.pulsus.com/journal-pharmacology-medicinal-chemistry.html
• 1e Albericio F, El-Faham A. Org. Process Res. Dev. 2018; 22: 760
• 2 Zarecki AP, Kolanowski JL, Markiewicz WT. Molecules 2020; 25: 1761
• 3a El-Faham A, Albericio F. J. Org. Chem. 2008; 73: 2731
• 3b Guo L, Jia S, Diercks CS, Yang X, Alshmimri SA, Yaghi OM. Angew. Chem. Int. Ed. 2020; 59: 2023
• 3c Philipova I, Stavrakov G, Dimitrov V, Vassilev N. THEOCHEM 2020; 1219: 128568
• 4a Kumishima M, Kawachi C, Morita J, Terao K, Iwasaki F, Tani S. Tetrahedron 1999; 55: 13159
• 4b Kunishima M, Yoshimura K, Morigaki K, Kawamata R, Terao K, Tani S. J. Am. Chem. Soc. 2001; 123: 10760
• 4c Kunishima M, Kawachi C, Hioki K, Terao K, Tani S. Tetrahedron 2001; 57: 1551
• 4d Scrivanti A, Bortoluzzi M, Sole R, Beghetto V. Chem. Pap. 2018; 72: 799
• 4e Scrivanti A, Sole R, Bortoluzzi M, Beghetto V, Bardella N, Dolmella A. Inorg. Chim. Acta 2019; 498: 119
• 5a Falchi A, Giacomelli G, Porcheddu A, Taddei M. Synlett 2000; 275
• 5b Kaminsky ZJ, Kolesinska B, Kolesinska J, Sabatino G, Chelli M, Rovero P, Błaszczyk M, Głowka ML, Papini AM. J. Am. Chem. Soc. 2005; 127: 16912
• 5c D’Este M, Eglin D, Alini M. Carbohydr. Polym. 2014; 108: 239
• 5d Hawkins PM. E, Giltrap AM, Nagalingam G, Britton WJ, Payne RJ. Org. Lett. 2018; 20: 1019
• 5e Hawkins PM. E, Tran W, Nagalingam G, Cheung CY, Giltrap A, Cook G, Britton W, Payne RJ. Chem. Eur. J. 2020; 26: 15200
• 6a Beghetto V, Agostinis L, Gatto V, Samiolo R, Scrivanti A. J. Cleaner Prod. 2019; 220: 864
• 6b Beghetto V, Gatto V, Conca S, Bardella N, Buranello C, Gasparetto G, Sole R. Carbohydr. Polym. 2020; 249: 116810
• 7 Petta D, Eglin D, Grijpma DW, D’Este M. Carbohydr. Polym. 2016; 151: 576
• 8a Sheldon RA. Green Chem. 2016; 18: 3180
• 8b Al Musaimi O, de la Torre BG, Albericio F. Green Chem. 2020; 22: 996
• 9a Paganelli S, Alam MM, Beghetto V, Scrivanti A, Amadio E, Bertoldini M, Matteoli U. Appl. Catal., A. 2015; 503: 20
• 9b Beghetto V, Scrivanti A, Bertoldini M, Aversa M, Zancanaro A, Matteoli U. Synthesis 2015; 47: 272
• 9c Sole R, Bortoluzzi M, Spannenberg A, Tin S, Beghetto V, de Vries JG. Dalton Trans. 2019; 48: 13580
• 10 Sole R, Taddei L, Franceschi C, Beghetto V. Molecules 2019; 24: 2979
• 11 Kaminski ZJ. Biopolymers 2000; 55: 140
• 12 Kunishima M, Ujigawa T, Nagaoka Y, Kawachi C, Hioki K, Shiro M. Chem. Eur. J. 2012; 18: 15856
• 13 Kitamura M, Sasaki S, Nishikawa R, Yamada K, Kunishima M. RSC Adv. 2018; 8: 22482
• 14a Hansch C, Leo A, Taft RW. Chem. Rev. 1991; 91: 165
• 14b Kunishima M, Kato D, Kimura N, Kitamura M, Yamada K, Hioki K. Beilstein J. Org. Chem. 2016; 12: 1897
• 15a Raw SA. Tetrahedron Lett. 2009; 50: 946
• 15b Loebel C, D’Este M, Alini M, Zenobi-Wong M, Eglin D. Carbohydr. Polym. 2015; 115: 235
• 16a Pelet JM, Putnam D. Bioconjugate Chem. 2011; 22: 329
• 16b Princz MA, Sheardown H. J. Biomater. Sci. Polym. Ed. 2012; 23: 2207
• 16c Taylor MM, Bumanlag LP, Brown EM, Liu C. J. Am. Leather Chem. Assoc. 2016; 111: 155
• 17a Tang HR, Covington AD, Hancock RA. J. Agric. Food Chem. 2003; 51: 6652
• 17b Yang C. Bull. Mater. Sci. 2012; 35: 913
• 17c Moon H, Choy S, Park Y, Jung YM, Koo YM, Hwang DS. Mar. Drugs 2019; 17: 318
• 17d Zhang Y, Snow T, Smith AJ, Holmes G, Prabakar S. Int. J. Biol. Macromol. 2019; 126: 123
• 18 Covington AD. Chem. Soc. Rev. 1997; 26: 111
• 19 Cui L, Qiang X. J. Renewable Mater. 2019; 7: 57; DOI: 10.32604/jrm.2019.00118.
• 20 Moktadir MdA, Ahmadi HB, Sultana R, Zohra FT, Liou JJ. H, Rezaei J. J. Cleaner Prod. 2020; 251: 119737
• 21 Yu L, Qiang X, Cui L, Chen B, Wang X, Wu X. J. Cleaner Prod. 2020; 270: 122351
• 22 Wu X, Qiang X, Liu D, Yu L, Wang X. J. Cleaner Prod. 2020; 270: 122399