ChemInform Abstract: Theophyllinylpyrimidine Scaffolds Undergo Intramolecular Cyclization Reactions to Form 1,3‐Diazepines and Imidazopurines.

Abstract

Theophyllinylpyrimidine Scaffolds Undergo Intramolecular Cyclization Reactions to Form 1,3-Diazepines and Imidazopurines. -(LEBEDYEVA*, I. O.; POVSTYANOY, V. M.; RYABITSKII, A. B.; PANASYUK, O.; IVAHNENKO, E.; LOZOVA, V. P.; MARKEVICH, I.; ALLAKHVERDOVA, S.; POVSTYANOY, V.; Eur. J. Org. Chem. 2013, 21, 4594-4606, http://dx.

Transformations of Di‐ and Tetrahydropyrimidine Derivatives into Condensed Heterocycles with Retention of their Partially Saturated Structure

“…For example, approach, which is based on bromination and a subsequent nucleophilic replacement reaction, is well documented. 6‐Bromo‐ and 6‐dibromomethyl‐3,4‐dihydropyrimidines are a versatile, readily accessible building blocks for the synthesis of furo[3,4‐ d ]pyrimidines , pyrrolo[3,4‐ d ]pyrimidines , pyrimido[4,5‐ d ]pyridazines , thiazolo[3,4‐ c ]pyrimidine , and cyclopenta[d]pyrimidine .…”

Theophyllinylpyrimidine Scaffolds Undergo Intramolecular Cyclization Reactions to Form 1,3‐Diazepines and Imidazopurines

“…Even though the biological and medicinal properties of both substituted theophyllines and pyrimidines are well known, the nucleophilicity of dihydropyrimidines is less well studied 13. The literature shows that upon reaction with nucleophiles, 6‐halogenomethylated pyrimidines undergo ring closure to form [3,4‐ d ]‐fused pyrroles,13a–13d furans,13a,13e and pyridazines 13c. The high reactivity of 2‐oxo‐4‐aryl‐5‐ethoxycarbonyl‐6‐halogenomethylpyrimidines towards nucleophiles is made possible by the halogen atom in the 6‐halogenomethyl group and the 5‐ethoxycarbonyl group on the pyrimidine core 13.…”

Synthesis of Tetracyclic 2,3-Dihydro-1,3-diazepines from a Dinitrodibenzothiophene Derivative

“…Since the last comprehensive survey of their synthesis 31 only a handful of new synthetic approaches have been reported for monocyclic, [32][33][34][35] singly- [36][37][38][39] or doubly-ringfused 1,3-diazepines. [40][41][42][43][44][45][46][47][48][49] In this work the introduction of sterically hindered nitro groups at the 1-and 9-positions of a dibenzothiophene-5,5-dioxide derivative provides access to a new two-electron accepting molecule, which is a precursor to luminescent four-ring-fused 2,3-dihydro-1,3-diazepines 6-8 using facile protocols in synthetically viable yields. To our knowledge these molecules represent the first examples of tetracyclic 1,3-diazepine derivatives.…”