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Functionalized C₃-Symmetric Building Blocks-The Chemistry of Triaminotrimesic Acid.

ABSTRACT: A series of C₃-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reactivity of these electronically sophisticated compounds was investigated by the formation of azides, the click reaction of the azides and a Sandmeyer-like reaction. Caused by the low stability of triaminobenzenes, direct N-alkylation was rarely reported. The use of the stable alkyl triamino-benzene-tricarboxylates allowed us total N-alkylation under standard alkylation conditions. The molecular structures of the C₃-symmetric structures have been corroborated by an X-ray analysis.

SUBMITTER: Schmidt L

PROVIDER: S-EPMC9322044 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Functionalized C3-Symmetric Building Blocks-The Chemistry of Triaminotrimesic Acid.

Schmidt Lisa L Wagner Danny D Nieger Martin M Bräse Stefan S

Molecules (Basel, Switzerland) 20220707 14

A series of C3-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reactivity of these electronically sophisticated compounds was investigated by the formation of azides, the click reaction of the azides and a Sandmeyer-like reaction. Caused by the low stability of triaminobenzenes, direct N ...[more]

PMID: 35889238

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