Efficient Copper‐Promoted Tandem Multi‐Component Strategy: The Synthesis of 1‐ Aryl/Alkyl‐5‐(<i>N</i>‐Benzoylamino) Tetrazoles and Guanidine's

Shaik, Baji; Seelam, Mohan; Tamminana, Ramana; Kammela, Prasad Rao

doi:10.1002/slct.201702568

Cited by 8 publications

(2 citation statements)

References 70 publications

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“…The literature-reported strategy was followed for the synthesis of BTCC and MBTB. 59 Accordingly, a solution of ammonium thiocyanate in anhydrous acetone (20 mL) was heated up to the boiling point, followed by the drop-wise addition of benzyl chloride. To this solution, the preheated 4-(aminomethyl)cyclohexane-1-carboxylic acid in acetone (in the case of compound BTCC) and methyl 2-aminobenzoate (in the case of MBTB) was added and stirred for 30 min and then poured in cold water.…”

Section: Methodsmentioning

confidence: 99%

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Single-Crystal Investigation, Hirshfeld Surface Analysis, and DFT Study of Third-Order NLO Properties of Unsymmetrical Acyl Thiourea Derivatives

et al. 2021

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In the current research work, unsymmetrical acyl thiourea derivatives, 4-((3-benzoylthioureido)methyl)cyclohexane-1-carboxylic acid (BTCC) and methyl 2-(3-benzoylthioureido)benzoate (MBTB), have been synthesized efficiently. The structures of these crystalline thioureas were unambiguously confirmed by single-crystal diffractional analysis. The crystallographic investigation showed that the molecular configuration of both compounds is stabilized by intramolecular N–H···O bonding. The crystal packing of BTCC is stabilized by strong N–H···O bonding and comparatively weak O–H···S, C–H···O, C–H···π, and C–O···π interactions, whereas strong N–H···O bonding and comparatively weak C–H···O, C–H···S, and C–H···π interactions are responsible for the crystal packing of MBTB. The noncovalent interactions that are responsible for the crystal packing are explored by the Hirshfeld surface analysis for both compounds. The void analysis is performed to find the quantitative strength of crystal packing in both compounds. Additionally, state-of-the-art applied quantum chemical techniques are used to further explore the structure–property relationship in the above-entitled molecules. The optimization of molecular geometries showed a reasonably good correlation with their respective experimental structures. Third-order nonlinear optical (NLO) polarizability calculations were performed to see the advanced functional application of entitled compounds as efficient NLO materials. The average static γ amplitudes are found to be 27.30 × 10–36 and 102.91 × 10–36 esu for the compounds BTCC and MBTB, respectively. The γ amplitude of MBTB is calculated to be 3.77 times larger, which is probably due to better charge-transfer characteristics in MBTB. The quantum chemical analysis in the form of 3-D plots was also performed for their frontier molecular orbitals and molecular electrostatic potentials for understanding charge-transfer characteristics. We believe that the current investigation will not only report the new BTCC and MBTB compounds but also evoke the interest of the materials science community in their potential use in NLO applications.

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Section: Methodsmentioning

confidence: 99%

“…The literature-reported strategy was followed for the synthesis of BTCC and MBTB . Accordingly, a solution of ammonium thiocyanate in anhydrous acetone (20 mL) was heated up to the boiling point, followed by the drop-wise addition of benzyl chloride.…”

Section: Methodsmentioning

confidence: 99%

Single-Crystal Investigation, Hirshfeld Surface Analysis, and DFT Study of Third-Order NLO Properties of Unsymmetrical Acyl Thiourea Derivatives

et al. 2021

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Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Yu,

Hao,

Liu

et al. 2024

Adv Synth Catal

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A one‐pot method has been developed for synthesizing diverse substituted 5‐aminotetrazoles via the electrochemically induced desulfurizative addition‐cyclization of thioureas with azidotrimethylsilane. This methodology enables the construction of C–N and N–N bonds under mild reaction conditions without transition metal catalysts or external oxidizing agents. The applicability of this approach is demonstrated by its broad substrate scope, compatibility with various functional groups, scalability to gram‐scale synthesis, and practicality evidenced by the synthesis of an antibacterial agent

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Copper‐catalyzed multicomponent green reaction approach: Synthesis of dihydropyrano [2,3‐c] pyrazoles and evaluation of their anti‐cancer activity

Kumar

Tamminana

2022

Journal of Heterocyclic Chem

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A facile, efficient, and simple one‐pot multi‐component protocol for the synthesis of pyrano[2,3‐c] pyrazoles has been developed using a cheap and readily available copper catalyst under moderate reaction conditions. Target products are obtained from aromatic aldehyde via Knoevenagel condensation and Michael addition reactions. Functional group tolerance and reaction mechanisms have also been examined in this methodology. In addition, we have also evaluated the anti‐cancer activity of the target products and we have attempted this method for practical utility purposes also.

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Efficient Copper‐Promoted Tandem Multi‐Component Strategy: The Synthesis of 1‐ Aryl/Alkyl‐5‐(N‐Benzoylamino) Tetrazoles and Guanidine's

Cited by 8 publications

References 70 publications

Single-Crystal Investigation, Hirshfeld Surface Analysis, and DFT Study of Third-Order NLO Properties of Unsymmetrical Acyl Thiourea Derivatives

Single-Crystal Investigation, Hirshfeld Surface Analysis, and DFT Study of Third-Order NLO Properties of Unsymmetrical Acyl Thiourea Derivatives

Electrochemically Induced Desulfurization of Thioureas for the Synthesis of Substituted 5‐Aminotetrazoles

Copper‐catalyzed multicomponent green reaction approach: Synthesis of dihydropyrano [2,3‐c] pyrazoles and evaluation of their anti‐cancer activity

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