Syntheses and crystal structure of 4-[(pyridin-3-yl)diazenyl]morpholine and 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2023-02, Vol.79 (2), p.74-78
• Main Authors: Sokhna, Seynabou, Seck, Insa, Thiam, Ibrahima El Hadj, Presset, Marc, Ndoye, Samba Fama, Ba, Lalla Aïcha, Samb, Issa, Coles, Simon, Orton, James, Seck, Matar, Le Gall, Erwan, Gaye, Mohamed
• Format: Article
• Language: English
• Subjects: 1,2,3,4-tetrahydroquinolein; 1,2,3-triazenes; crystal structure; morpholine; pyridine
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989023000129

Two new heterocyclic 1,2,3-triazenes were synthesized by diazotation of 3-aminopyridine following respectively by coupling with morpholine or 1,2,3,4-tetrahydroquinoline. 4-[(Pyridin-3-yl)diazenyl]morpholine ( I ), C 9 H 12 N 4 O, has monoclinic P 2 1 / c symmetry at 100 K, while 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline ( II ), C 14 H 14 N 4 , has monoclinic P 2 1 / n symmetry at 100 K. These 1,2,3-triazene derivatives were synthesized by the organic medium method by coupling reactions of 3-aminopyridine with morpholine and 1,2,3,4-tetrahydroquinoline, respectively, and characterized by 1 H NMR, 13 C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The molecule of compound I consists of pyridine and morpholine rings connected by an azo moiety (–N=N–). In the molecule of II , the pyridine ring and the 1,2,3,4-tetrahydroquinoline unit are also connected by an azo moiety. The double- and single-bond distances in the triazene chain are comparable for the two compounds. In both crystal structures, the molecules are connected by C—H...N interactions, forming infinite chains for I and layers parallel to the bc plane for II .