Synthesis of heterofunctional 1,3,7-triazapyrene derivatives by SNH and SNAr reactions

Боровлев, И. В.; Демидов, О. П.; Kurnosova, Nadezhda A.; Avakyan, Elena K.; Амангазиева, Гульминат А.

doi:10.1134/s1070428015100140

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2021

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“…The reaction of 1,3,7-triazapyrene ( 3 ) with electron-rich arenes in concentrated hydrochloric acid yields a limited amount of 6-aryl-1,3,7-triazapyrenes (Scheme , route B) . Oxidative nucleophilic alkoxylation (Scheme , route C) and (alkyl)amination (Scheme , routes D (S N H ) and E have also been examined to deliver C(6)-heterosubstituted 1,3,7-triazapyrenes. Interestingly, only the C(6)-regioisomer has been obtained for those examples.…”

Section: Introductionsupporting

confidence: 85%

1,3,7-Triazapyrene-Basedortho-Carborane Fluorophores: Convenient Synthesis, Theoretical Studies, and Aggregation-Induced Emission Properties

et al. 2021

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A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SN H), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SN H transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects.

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Section: Introductionsupporting

confidence: 85%