Tetrazoles: XLVIII. 3H-Naphtho[2,1-e]-and 3H-Naphtho[1,2-e][1,2,4]triazepines from 5-Aryltetrazoles. Physical and Chemical Properties

Abstract

Thermolysis of N-imidoyltetrazoles generated under conditions of phase-transfer catalysis from 5-aryltetrazoles and N-(2-naphthyl)benzimidoyl chloride yields 3H-naphtho[2,1-e][1,2,4]triazepines, and acid hydrolysis of the latter leads to formation of 3-arylbenz[e]indazoles. Acid hydrolysis of 3H-naphtho[1,2-e]-[1,2,4]triazepine gives the corresponding amino ketone. * For communication XLVII, see [1].

Advances in 1,2,4-triazepines chemistry

“…Acid hydrolysis of the pyrido(benzo)[3,2-e][1,2,4]triazepines 84a, b led to the corresponding amino ketones 323 and benzoic acid (Scheme 81). 59,116 Hydrolysis of naphthotriazepines 87a-c gave 324a-c, which means that their structures synthesized previously from 5-aryltetrazoles and N-(2-naphthyl) benzimidoyl chlorides correspond to this isomer (Scheme 82). 59 The acid hydrolysis of triazepine 87d afforded in a good yield the corresponding amino ketone 325 and benzoic acid (Scheme 83).…”

“…59,116 Hydrolysis of naphthotriazepines 87a-c gave 324a-c, which means that their structures synthesized previously from 5-aryltetrazoles and N-(2-naphthyl) benzimidoyl chlorides correspond to this isomer (Scheme 82). 59 The acid hydrolysis of triazepine 87d afforded in a good yield the corresponding amino ketone 325 and benzoic acid (Scheme 83). 59 Alcoholysis of 4-methyl-3H-benzo[e][1,2,4]triazepin-5(4H)one (100a) in ethoxide gave 3-(methylamino)quinazolin-4(3H)one (326) (Scheme 84).…”

“…59 The acid hydrolysis of triazepine 87d afforded in a good yield the corresponding amino ketone 325 and benzoic acid (Scheme 83). 59 Alcoholysis of 4-methyl-3H-benzo[e][1,2,4]triazepin-5(4H)one (100a) in ethoxide gave 3-(methylamino)quinazolin-4(3H)one (326) (Scheme 84). 54…”

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

“…The tetrazole‐based drugs possess various biological activities such as anti‐inflammatory, antiviral, antiallergic, antifungal, antibacterial, antiulcer, anticonvulsant and antitubercular activities, and have shown promising results in treatment of dreadful diseases, such as cancer and AIDS . In addition, they have important roles in coordination chemistry as a ligand for preparation of complex heterocyclic structures . Various methods have been reported for the synthesis of 5‐substituted 1 H ‐tetrazoles, which most of them are based on the addition of trimethylsilyl azide or sodium azide to nitrile group.…”