Synthesis of New 1,3a,6,6a-Tetraazapentalene Derivatives under Cadogan Reaction Conditions

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Abstract

A convenient synthetic approach has been developed for novel monobenzotriazoles incorporating a mesoionic 1,3a,6,6a-tetraazapentalene core. The method involves a Cu(I)-catalyzed (3+2) cycloaddition of ortho-nitrophenyl azide to terminal aryl(alkyl)acetylenes, followed by an intramolecular cyclization under Cadogan-type deoxygenation conditions. The process can be successfully performed in a one-pot fashion, affording the target benzo[d][1,2,3]triazolo[1,2-a]triazole derivatives in good yields.

About the authors

P. S. Gribanov

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences; Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: gribanovps@mail.ru
ORCID iD: 0000-0003-3820-5442
Moscow, Russia; Moscow, Russia

A. N. Philippova

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

ORCID iD: 0000-0002-6108-5103
Moscow, Russia

M. A. Topchiy

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

ORCID iD: 0000-0002-6604-7034
Moscow, Russia

A. F. Smol’yakov

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

ORCID iD: 0000-0002-7228-7093
Moscow, Russia

D. V. Vorobyeva

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

ORCID iD: 0000-0002-7325-6504
Moscow, Russia

A. N. Rodionov

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

ORCID iD: 0000-0001-9227-7434
Moscow, Russia

A. F. Asachenko

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

ORCID iD: 0000-0001-8638-9261
Moscow, Russia

S. N. Osipov

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: osipov@ineos.ac.ru
ORCID iD: 0000-0001-5625-776X
Moscow, Russia

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