• Bulletin of the Korean Chemical Society
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• v.32 no.11
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• pp.4001-4004
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• 2011

Various 5-substituted 1H-tetrazole derivatives were synthesized in a simple and environmentally benign method from the reaction of aryl and benzyl nitriles with sodium azide in solvent-free media using montmorillonite K-10 clay as solid recyclable heterogeneous acidic catalyst and microwave irradiation in good yields and short reaction times.

• Biomolecules & Therapeutics
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• v.30 no.2
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• pp.191-202
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• 2022

Tetrazoles were designed and synthesized as potential inhibitors of triple monoamine neurotransmitters (dopamine, norepinephrine, serotonin) reuptake based on the functional and docking simulation of compound 6 which were performed in a previous study. The compound structure consisted of a tetrazole-linker (n)-piperidine/piperazine-spacer (m)-phenyl ring, with tetrazole attached to two phenyl rings (R1 and R2). Altering the carbon number in the linker (n) from 3 to 4 and in the spacer (m) from 0 to 1 increased the potency of serotonin reuptake inhibition. Depending on the nature of piperidine/piperazine, the substituents at R1 and R2 exerted various effects in determining their inhibitory effects on monoamine reuptake. Docking study showed that the selectivity of tetrazole for different transporters was determined based on multiple interactions with various residues on transporters, including hydrophobic residues on transmembrane domains 1, 3, 6, and 8. Co-expression of dopamine transporter, which lowers dopamine concentration in the biophase by uptaking dopamine into the cells, inhibited the dopamine-induced endoctytosis of dopamine D₂ receptor. When tested for compound 40 and 56, compound 40 which has more potent inhibitory activity on dopamine reuptake more strongly disinhibited the inhibitory activity of dopamine transporter on the endocytosis of dopamine D₂ receptor. Overall, we identified candidate inhibitors of triple monoamine neurotransmitter reuptake and provided a theoretical background for identifying such neurotransmitter modifiers for developing novel therapeutic agents of various neuropsychiatric disorders.

• Bulletin of the Korean Chemical Society
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• v.32 no.2
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• pp.547-552
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• 2011

Azido contained polymers were treated with various substituted N-propargyl tetrazoles in $CH_2Cl_2/H_2O$ at room temperature by Cu-catalyzed [2+3] cycloaddition to afford high yields of the corresponding polymers, possessing both triazole and tetrazole moiety.

• Journal of the Korea Institute of Military Science and Technology
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• v.20 no.6
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• pp.781-787
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• 2017

A new method for synthesizing the tetrazole derivatives from secondary amines through cyanation/tetrazolation has been developed. Trichloroacetonitrile is used as the cyano source to synthesize N-nitrile instead of highly toxic and expensive cyanogen bromide. In this protocol, the reaction of secondary amines with various substituents proceed smoothly, and the desired tetrazole derivatives are obtained directly in fair to high yields without isolation of intermediate cyanamides.

• Proceedings of the Korean Vacuum Society Conference
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• 2011.08a
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• pp.207-207
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• 2011

Aromatic nitriles possess versatile utilities and are indispensible not only in organic synthesis but also in chemical industry. In fact, the nitrile group is an important precursor for various functional groups such as aldehydes, amines, amidines, tetrazoles, amides, and their carboxyl derivatives. Representative methods for the preparation of organonitriles with cyanide-containing reagents are the Sandmeyer and Rosenmund-von Braun reactions. Recently, a catalytic route to aryl nitriles has been reported on the basis of the chelation-assisted C-H bond activation or metal-catalyzed cyanation of haloarenes. In those cyanation protocols, the "CN" unit is provided from metal-bound precursors of MCN (M=Cu, K, Na, Zn), TMSCN, or K3Fe(CN)6. Additionally, it can be generated in situ from nitromethane or acetone cyanohydrin. Herein, we report the first example of generating "CN" from two different, readily available precursors, ammonia and N,N-dimethylformamide (DMF). In addition, its synthetic utility is demonstrated through the Pd-catalyzed cyanation of arene C-H bonds.