New 1H-1-alkyl-6-methyl-3-phenyl-7-phenylazo-pyrazolo[5,1-c][1,2,4]triazoles through regioselective alkylation of 1H-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles

Abstract1H-1-Alkyl-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles (2aa-ad) were obtained by regioselective alkylation of 1H-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles (2a). 1H-1-Alkyl-6-methyl-3-phenyl-7-phenylazopyrazolo[5,1-c][1,2,4]triazoles 2aa and 2ab were also prepared by coupling phenyldiazonium chloride with 1H-1-alkyl-6-methyl-3-phenyl-pyrazolo[5,1-c][1,2,4]triazoles 1aa and 1ab. The new compounds were characterized by IR, UV-VIS, 1H-NMR, 13C-NMR, and 15N-NMR spectroscopy and their structures and actual tautomeric forms were established unequivocally.

Download Full-text

Unexpected Keto-enol Tautomerism in the Cyclopyridinophane Class Direct and indirect proofs

Revista de Chimie ◽

10.37358/rc.08.10.1973 ◽

2008 ◽

Vol 59 (10) ◽

Author(s):

Paul Ionut Dron ◽

Neculai Doru Miron ◽

Gheorghe Surpateanu

Keyword(s):

Nmr Spectroscopy ◽

1H Nmr ◽

Stable Conformer ◽

Ph Measurements ◽

Theoretical Methods ◽

Nmr Data ◽

Tautomeric Forms ◽

New Compounds

The paper presents the synthesis of cyclo (bis-paraquat p-phenylene p-phenylene-carbonyl) tetrakis (hexafluorophosphate), named �CETOBOX�, and the closely related structural determinations. This compound exists in three tautomeric forms. These forms were evidentiated by NMR-data (1H-NMR, TOCSY, COSY, NOESY), UV-Vis spectra coupled with pH measurements and by synthesis. As the �CETOBOX� gives �in situ� only the corresponding monoylide, the synthesis of a new fluorescent indolizine cyclophane has been performed by a 3+2 cycloaddition. All structures of the new compounds presented herein have been established by NMR spectroscopy. Also, theoretical methods (MM3, AM1, AM1-COSMO and B88LYPDFT) have been used to determine the most stable conformer structures.

Download Full-text

New Heterocyclic Compounds from 1,2,4-triazoles Class with Potential Cytotoxic Activity

Revista de Chimie ◽

10.37358/rc.17.11.5916 ◽

2017 ◽

Vol 68 (11) ◽

pp. 2503-2508 ◽

Cited By ~ 1

Author(s):

Laura Ileana Socea ◽

Stefania Felicia Barbuceanu ◽

Bogdan Socea ◽

Constantin Draghici ◽

Theodora Venera Apostol ◽

...

Keyword(s):

Nmr Spectroscopy ◽

Cytotoxic Activity ◽

Spectral Data ◽

1H Nmr ◽

Elemental Analysis ◽

13C Nmr ◽

Heterocyclic Compounds ◽

Cytotoxic Effect ◽

13C Nmr Spectroscopy ◽

New Compounds

Acylhydrazinecarbothioamides (2a,b) were synthesized by addition of 2-(5H-dibenzo[a,d][7]annulen-5-yl)acetohydrazide to different isothiocyanates. The new 1,2,4-triazol-3-thioles (3a,b) were synthesized by cyclization of new 2- acylhydrazinecarbothioamides (3a,b) in basic media. Alkylation of 1,2,4-triazole-3-thiols (3a-c) with ethyl bromide gave only S-substituted derivatives (4a-c). The structures of the synthesized compounds have been established on spectral data (IR, 1H-NMR and 13C-NMR spectroscopy) and elemental analysis. The cytotoxic effect of new compounds was evaluated using two alternative models on plant and invertebrate organisms.

Download Full-text