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DOI: 10.1055/s-0042-1751494
Synthesis and Characterization of an Eight-Membered Heterocyclic 1,3,5,7-Tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane
Abstract
N,N′-Bis(3-pyridyl)methanediamine was prepared by treating 3-aminopyridine with formaldehyde in acetonitrile. By treating it with formaldehyde, the eight-membered heterocyclic ring compound 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was prepared. This could occur in a two-step manner in a [3+1+3+1] cycloaddition reaction. The compounds were characterized by X-ray crystallography, 1H and 13C NMR spectroscopy, and mass spectrometry. The powder XRD pattern of 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane was also determined and revealed an uncommon twist-crown conformation, which was further confirmed by DFT calculations.
Key words
N,N′-bis(3-pyridyl)methanediamine - 1,3,5,7-tetra(3-pyridyl)-1,3,5,7-tetrazacyclooctane - heterocycles - cyclooctanes - cycloaddition - twist-crown conformation - DFT calculationsSupporting Information
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article is available online at https://doi.org/10.1055/s-0042-1751494.
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Publication History
Received: 26 July 2023
Accepted after revision: 18 August 2023
Article published online:
16 October 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1 Petasis NA, Patane MA. Tetrahedron 1992; 48: 5757
- 2 Drexler C, Paulus H, Elias H. Inorg. Chem. 1991; 30: 1297
- 3 Arbuckle BW, Bharadwaj PK, Musker WK. Inorg. Chem. 1991; 30: 440
- 4 Kolar GF, Schendzielorz M. Tetrahedron Lett. 1985; 26: 1043
- 5 Zhao L.-L, Wan Y, Huang S.-Y, Chen L.-F, Liu G.-X, Zhang W.-L, Yue S.-N, Wu H. Z. Kristallogr. NCS 2004; 229: 23
- 6 Kakanejadifard A, Mahmodi L, Yari A, Mohajeri A. J. Heterocycl. Chem. 2006; 43; 1696
- 7 Akhmetova VR, Niatshina ZT, Khabibullina GR, Bushmarinov IS, Borisova AO, Starikova ZA, Korzhova LF, Kunakova RV. Russ. Chem. Bull. Int. Ed. 2010; 59; 1002
- 8 Schweizer EE, Hayes JE, Rheingold A, Wei X. J. Org. Chem. 1987; 52: 1810
- 9 Lin H, Zhu S.-G, Li H.-Z, Peng X.-H. J. Mol. Struct. 2013; 1048: 339
- 10 Landenberger KB, Matzger AJ. Cryst. Growth Des. 2012; 12: 3603
- 11 Bolton O, Simke LR, Pagoria PF, Matzger AJ. Cryst. Growth Des. 2012; 12: 4311
- 12 Zhurova EA, Zhurov VV, Pinkerton AA. J. Am. Chem. Soc. 2007; 129: 13887
- 13 Deschamps JR, Frisch M, Parrish D. J. Chem. Crystallogr. 2011; 41: 966
- 14 Randaccio L, Zangrand E, Gei MH, Giumanini AG. J. Prakt. Chem. 1987; 329: 187
- 15 Li L, Li H.-Y, Ren Z.-G, Lang J.-P. Eur. J. Inorg. Chem. 2014; 824
- 16 Li L. Chin. J. Inorg. Chem. 2021; 37: 121
- 17 Bruker APEX2, SAINT, and SADABS. Bruker AXS Inc; Madison (WI): 2009
- 18 Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3
- 19 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
- 20 Akhmetova VR, Nadyrgulova GR, Niatshina ZT, Dzhemilev UM. Chem. Heterocycl. Compd. 2009; 45: 1155
- 21 Akhmetova VR, Nadyrgulova GR, Khafizova SR, Tyumkina TV, Yakovenko AA, Antipin MY, Khalilov LM, Kunakova RV, Dzhemilev UM. Russ. Chem. Bull. Int. Ed. 2006; 55: 312
- 22 Becke AD. J. Chem. Phys. 1993; 98: 1372
- 23 Lee CT, Yang WT, Parr RG. Phys. Rev. B 1988; 37: 785