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Updated: Jun 2, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
2,6-Bis(2-methyl-1,3-diazinan-2-yl)pyridine
Abstract:
The title compound, C(15)H(25)N(5), is an aminalization product between 2,6-diacetyl-pyridine and 1,3-diamino-propane. It crystallizes with two independent mol-ecules in the asymmetric unit with different conformations. In the first mol-ecule, the methyl groups are cis oriented with respect to the pyridine ring [N-C-C-C torsion angles = 72.5 (1) and 80.3 (1)°], while they are trans oriented in the second mol-ecule [N-C-C-C torsion angles = 82.6 (1) and -90.8 (1)°]. Each of the two mol-ecules forms centrosymmetric dimers held together by N-H⋯N hydrogen bonds, thus forming R(2) (2)(16) rings. The two dimers are inter-linked by additional N-H⋯N bonds into R(4) (4)(14) rings, building chains along the a axis. These patterns influence the orientation (either equatorial or axial) of the N-H bonds.
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