Synthetic Routes towards Thiazolo[1,3,5]triazines (Review)

Dolzhenko, Anton V.

doi:10.3987/rev-10-687

Cited by 12 publications

(1 citation statement)

References 71 publications

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“…As a consequence, development of synthetic methods to access fused 1,3,5‐triazines is of great importance to biomedical research. To date, various synthetic methods have been developed for the construction of s ‐triazine‐fused bicyclic frameworks with triazoles, pyrazoles or thiazoles –. However, synthetic approaches to 1,3,5‐triazino[1,2‐ a ]benzimidazoles have been reported only rarely, and disadvantages associated with the existing methods include harsh reaction conditions and limited substrate scope.…”

Section: Reaction Conditions Optimization For the Synthesis Of 135‐mentioning

confidence: 99%

Iodine/Copper(I)‐Catalyzed Direct Annulation of N‐Benzimidazolyl Amidines with Aldehydes for the Synthesis of Ortho‐Fused 1,3,5‐Triazines

et al. 2017

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A direct annulation reaction of N-benzimidazolyl amidines with aldehydes has been established and allows the synthesis of ortho-fused 1,3,5-triazine derivatives. The N-benzimidazolyl amidine substrates are readily accessible by the addition of 2-aminobenzimidazoles to the corresponding nitriles. In the presence of molecular iodine and copper iodide, cyclization of benzimidazolyl amidines with various aldehydes in toluene under reflux followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) gives the corresponding products. In this reaction, iodine acts more as a Lewis acid catalyst than as an oxidant. This synthetic process is insensitive to air and operationally simple, and provides facile access to a variety of novel 1,3,5-triazino[1,2-a]benzimidazoles and related heterocycles.

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Section: Reaction Conditions Optimization For the Synthesis Of 135‐mentioning

confidence: 99%