SYNTHESIS OF NOVEL N-SUBSTITUTED AMPHIONIC MELAMINES WITH THE TANDEM 4-(1-CARBOXY-n-ALKOXY)PHENYL / 4-(n-OCTYLOXY)PHENYL UNITS AS POTENTIAL DENDRITIC BUILDING-BLOCKS

Stefania IONESCU-ZINCA; Pedro LAMEIRAS; Dan PORUMB; Emese GÁL; Mircea DARABANTU

doi:10.24193/subbchem.2020.1.04

SYNTHESIS OF NOVEL N-SUBSTITUTED AMPHIONIC MELAMINES WITH THE TANDEM 4-(1-CARBOXY-n-ALKOXY)PHENYL / 4-(n-OCTYLOXY)PHENYL UNITS AS POTENTIAL DENDRITIC BUILDING-BLOCKS

Authors

Stefania IONESCU-ZINCA Babeş-Bolyai University, Department of Chemistry, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania
Pedro LAMEIRAS University of Reims Champagne-Ardenne, ICMR, UMR 7312, BP 1039, 51687 Reims, France https://orcid.org/0000-0001-8416-750X
Dan PORUMB Babeş-Bolyai University, Department of Chemistry, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania
Emese GÁL Babeş-Bolyai University, Department of Chemistry and Chemical Engineering, Hungarian Line of Study, 11 Arany János St., 400028 Cluj-Napoca, Romania https://orcid.org/0000-0003-4324-0787
Mircea DARABANTU Babeş-Bolyai University, Department of Chemistry, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania. *Corresponding author: darab@chem.ubbcluj.ro

DOI:

https://doi.org/10.24193/subbchem.2020.1.04

Keywords:

(4-aminophenoxy)acetic acid, 4-(4-aminophenoxy)butyric acid, amphionic melamines, N-Boc-piperazine, 4-(n-octyloxy)aniline

Abstract

Starting from etheric type derivatives of 4-aminophenol, namely (4-aminophenoxy)acetic acid or 4-(4-aminophenoxy)butyric acid and 4-(n-octyloxy)aniline, we report herein two routes of access to two novel N-substituted amphionic melamines with the tandem 4-(1-carboxy-n-alkoxy) phenyl/4-(n-octyloxy)phenyl units against the piperazin-1-yl group, as a basic site. The successful S_N2-Ar aminations of cyanuric chloride performed with these amine-nucleophiles are discussed in terms of chemoselectivity, mainly in the third step of the synthesis, implying piperazine as such or its N-Boc-mono-protected form. The amphionic nature of the targeted melamines was fully confirmed both in solution (VT-NMR) and in the solid state (IR).

References

D. Abraham; P. E. Kennedy; A. S. Mehanna; D. C. Patwa; F. L. Williams; J. Med. Chem., 1984, 27, 967-978

Y. Katsura; T. Tomishi; Y. Inoue; K. Sakane; Y. Matsumoto; C. Morinaga; H. Ishikawa; H. Takasugi; J. Med. Chem., 2000, 43, 3315-3321

B. D. Palmer; J. B. Smaill; G. W. Rewcastle; E. M. Dobrusin; A. Kraker; C. V. Moore; R. W. Steinkampf; W. Dennya; Bioorg. Med. Chem. Lett., 2005, 15, 1931-1935

K. Hidaka; T. Kimura; A. J. Ruben; T. Uemura; M. Kamiya; A. Kiso; T. Okamoto; Y. Tsuchiya; Y. Hayashi; E. Freire; Y. Kiso; Bioorg. Med. Chem., 2008, 16, 10049-10060

R. Kumar; S. Jain; N. Jain; Der Pharma Chem., 2013, 5, 73-78

a) C. Morar; L. Cost; P. Lameiras; C. Antheaume; M. Darabantu; Synthetic Commun., 2015, 45, 1688-1695; b) C. Morar; P. Lameiras; A. Bende; G. Katona; E. Gál; M. Darabantu; Beilstein J. Org. Chem., 2018, 14, 1704-1722

C. Sacalis; C. Morar; P. Lameiras; A. Lupan; R. Silaghi-Dumitrescu; A. Bende; G. Katona; D. Porumb; D. Harakat; E. Gál; M. Darabantu; Tetrahedron, 2019, 75, 1-18

a) T. Okuno; A. Izuoka; T. Ito; S. Kubo; T. Sugawara; N. Sato; Y. Sugawara; J. Chem. Soc., Perkin Trans. 2, 1998, 4, 889-896; b) D. De Murillas Lopez; R. Pinol; M. B. Ros; J. L. Serrano; T. Sierra; M. R. De La Fuente; J. Mat. Chem., 2004, 14, 1117-1127; c) W. Li; W. Bu; H. Li; L. Wu; M. Lib; Chem. Commun., 2005, 30, 3785-3787; d) M. J. Jeong; J. H. Park; C. Lee; J. Y. Chang; Org. Lett., 2006, 8, 2221-2224

a) S. Yagai; M. Usui; T. Seki; H. Murayama; Y. Kikkawa; S. Uemura; T. Karatsu; A. Kitamura; A. Asano; S. Seki; J. Am. Chem. Soc., 2012, 134, 7983-7994; b) Z. Shi; H. Lu; Z. Chen; R. Cheng; D. Chen; Polymer, 2012, 53, 359-369; c) D. -Y Kim; S. -A. Lee; Y. -J. Choi; S. -H. Hwang; S. -W. Kuo; C. Nah; M. -H. Lee; K. -U. Jeong; Chem. Eur. J., 2014, 20, 5689-5695

See, for example: a) F. Popa; P. Lameiras; O. Moldovan; M. Tomoaia-Cotisel; E. Hénon; A. Martinez; C. Sacalis; A. Mocanu; Y. Ramondenc; M. Darabantu; Tetrahedron, 2012, 68, 8945-8967; b) O. Moldovan; I. Nagy; P. Lameiras; C. Antheaume; C. Sacalis; M. Darabantu; Tetrahedron: Asymmetry, 2015, 26, 683-701; c) C. Morar; G. Turdean; A. Bende; P. Lameiras; C. Antheaume; L. M. Muresan; M. Darabantu; C. R. Chimie, 2017, 20, 402-414

a) A. P. Umali; H. L. Crampton; E. E. Simanek; J. Org. Chem., 2007, 72, 9866-987; b) S. A. Bell; M. E. McLean; S. -K. Oh; S. E. Tichy; W. Zhang; R. M. Corn; R. M. Crooks; E. E. Simanek; Bioconjugate Chem., 2003, 14, 488-493

a) L. L. Lai; L. Y. Wang; C. H. Lee; Y. C. Lin; K. L. Cheng; Org. Lett., 2006, 8, 1541-1544; b) L. L. Lai; C. H. Lee; L. Y. Wang; K. L. Cheng; H. F. Hsu; J. Org. Chem., 2008, 73, 485-490

a) A. Chouai; V. J. Venditto; E. E. Simanek; Org. Synth., 2009, 86, 141-150; b) S. Ricken; P. W. Osinski; P. Eilbracht; R. Haag; J. Mol. Catal. A: Chem., 2006, 257, 78-88

a) T. Drakenberg; S. Forsen; Chem. Commun., 1971, 21, 1404-1405; b) S. S. Mirvish; P. Gannett; D. M. Babcook; D. Williamson; S. C. Chen; D. D. Weisenburger; J. Agric. Food Chem., 1991, 39, 1205-1210; c) A. R. Katritzky; I. Ghiviriga; D. C. Oniciu; A. J. Barkock; J. Chem. Soc. Perkin Trans. 2, 1994, 4, 785-792; d) A. R. Katritzky; I. Ghiviriga; P. G. Steel; D. C. Oniciu; J. Chem. Soc. Perkin Trans. 2, 1996, 3, 443-447; e) I. Ghiviriga; D. C. Oniciu; Chem. Commun., 2002, 22, 2718-2719

a) H. Friebolin in Basic One- and Two Dimensional NMR Spectroscopy; VCH Verlagsgesellschaft: Weinheim, New York, 1991; pp 147-165, 263-291; b) E. L. Eliel; H. S. Wilen in Stereochemistry of the Organic Compounds; John Wiley & Sons, New York, 1994; pp. 642

E. Fedeli; S. Hernández-Aínsa; A. Lancelot; R. González-Pastor; P. Calvo; T. Sierra; J. L. Serrano; Soft Matter 2015, 11, 6009-6017

M. A. van Dongen; B. G. Orr; M. M. Banaszak; J. Phys. Chem. B, 2014, 118, 7195-7202

A. R. Deac; C. Morar; G. L. Turdean; M. Darabantu; E. Gál; A. Bende; L. M. Muresan; J. Solid State Electrochem., 2016, 20, 3071-3081

a) F. S. Parker in Applications of Infrared Spectroscopy in Biochemistry, Biology and Medicine; Plenum Press, New-York, 1971; pp. 35; b) R. M. Silverstein; F. X. Webster; D. J. Kiemle in Identification Spectrométrique de Composés Organiques; De Boeck & Larcier s.a., 2007; pp. 95, 96, 101

R. A. Heacock; L. Marion; Can. J. Chem.; 1956, 34, 1782-1995

STUDIA UBB CHEMIA, Volume 65 (LXV), No. 1, March 2020

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Published

2020-03-20

How to Cite

IONESCU-ZINCA, S., LAMEIRAS, P., PORUMB, D., GÁL, E., & DARABANTU, M. (2020). SYNTHESIS OF NOVEL N-SUBSTITUTED AMPHIONIC MELAMINES WITH THE TANDEM 4-(1-CARBOXY-n-ALKOXY)PHENYL / 4-(n-OCTYLOXY)PHENYL UNITS AS POTENTIAL DENDRITIC BUILDING-BLOCKS . Studia Universitatis Babeș-Bolyai Chemia, 65(1), 39–54. https://doi.org/10.24193/subbchem.2020.1.04