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Updated: Aug 9, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Syntheses and crystal structure of 4-[(pyridin-3-yl)diazen-yl]morpholine and
Seynabou Sokhna1, Insa Seck1, Ibrahima El Hadj Thiam2
1Laboratoire de Chimie Organique et Thérapeutique, Faculté de Médecine, de Pharmacie et Odontologie, Université Cheikh Anta, Diop de Dakar, BP 5005, Dakar-Fann, Senegal.
Abstract:
Two new heterocyclic 1,2,3-triazenes were synthesized by diazo-tation of 3-amino-pyridine following respectively by coupling with morpholine or 1,2,3,4-tetra-hydro-quinoline. 4-[(Pyridin-3-yl)diazen-yl]morpholine (I), C9H12N4O, has monoclinic P21/c symmetry at 100 K, while 1-[(pyridin-3-yl)diazen-yl]-1,2,3,4-tetra-hydro-quinoline (II), C14H14N4, has monoclinic P21/n symmetry at 100 K. These 1,2,3-triazene derivatives were synthesized by the organic medium method by coupling reactions of 3-amino-pyridine with morpholine and 1,2,3,4-tetra-hydro-quinoline, respectively, and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The mol-ecule of compound I consists of pyridine and morpholine rings connected by an azo moiety (-N=N-). In the mol-ecule of II, the pyridine ring and the 1,2,3,4-tetra-hydro-quinoline 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 mol-ecules are connected by C-H⋯N inter-actions, forming infinite chains for I and layers parallel to the bc plane for II.
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