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Green and efficient synthesis of 1 H ‐indazolo[1,2‐ b ] phthalazine‐1,6,11(13 H )‐triones using ZrO(NO 3 ) 2 .2H 2 O as a novel catalyst and theoretical study of synthesized compounds
Author(s) -
Saberi Biroon Shabnam,
Shajari Nahid,
Yahyaei Hooriye
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3959
Subject(s) - chemistry , phthalazine , carbon 13 nmr , chemical shift , molecular orbital , computational chemistry , basis set , dimedone , ionization energy , elemental analysis , molecule , ionization , density functional theory , organic chemistry , catalysis , ion
The one‐pot three‐component synthesis for the preparation of 1 H ‐indazolo[1,2‐ b ] phthalazine‐1,6,11(13 H )‐triones through condensation of phthalimide, hydrazine monohydrate, dimedone, and aromatic aldehydes in the presence of a novel catalytic amount of ZrO(NO 3 ) 2 .2H 2 O at reflux conditions in water has been reported. Quantum theoretical calculations for the three structures of compounds ( 5a , 5b , and 5c ) were performed using the G3MP2, LC‐ωPBE, MP2, and B3LYP methods with the 6‐311 + G** basis set. After optimizing the structures, geometric parameters were obtained and experimental measurements were compared with the calculated data. The structures of the products were confirmed by IR, 1 H NMR, 13 C NMR, and elemental analysis. IR spectra data and 1 H NMR and 13 C NMR chemical shifts computations of the 1 H ‐indazolo[1,2‐ b ]phthalazine‐1,6,11(13 H )‐trione derivatives in the ground state were calculated. Frontier molecular orbitals, total density of states, thermodynamic parameters, and molecular electrostatic potentials of the title compounds were investigated by theoretical calculations. Molecular properties such as the ionization potential ( I ), electron affinity ( A ), chemical hardness ( η ), electronic chemical potential ( μ ), and electrophilicity ( ω ) were investigated for the structures. Consequently, there was an excellent agreement between experimental and theoretical results.