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Various 5‐substituted‐1H‐tetrazoles were synthesized via two strategies; direct [3+2] cycloaddition of substituted aryl nitriles with sodium azide, and tri‐component reaction of aldehydes, hydroxylamine hydrochloride with sodium azide in dimethylformamide (DMF) by applying M2(BDC)2(DABCO) [M: Cu, Co and Ni, BDC=1, 4‐benzenedicarboxylic acid, and DABCO= 1,4‐diazabicyclo[2.2.2]octane] as heterogeneous catalyst. Short reaction time, high yield, totally straightforward procedure and easy work‐up, as well as preparing tetrazole derivatives via relatively cheap and easily available aldehydes (in three‐component method) are some beneficial features of mentioned methodologies. It was found that among three studied transition metals, copper has a unique advantage over other metals in formation of the desired product.

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Solvent-free ball-milling synthesized porous metal-organic framework Cu2(BDC)2(DABCO) (BDC: benzene-1,4-dicarboxylic acid, DABCO: 1,4-diazabicyclo [2.2.2]octane) has been proved to be a practical catalyst for facile and convenient synthesis of 1,2,3-triazole derivatives via multicomponent reaction of terminal alkynes, benzyl or alkyl halides, and sodium azide in ethanol. Avoidance of usage and handling of hazardous organic azides, using ethanol as an easily available solvent, and simple preparation and recycling of the catalyst make this procedure a truly scale-up-able one. The high loading of copper ions in the catalyst leads to e cient catalytic activity and hence, its low-weight usage in reaction. The catalyst was recycled and reused several times without signi cant loss of its activity. Furthermore, novel derivatives were examined to investigate their potential antimicrobial activity via microdilution method.

Acylals can be prepared very fast and in excellent yields by the direct condensation of aldehydes with acetic anhydride under solvent-free condition by employing of MCM-41-SO 3 H as heterogeneous catalyst at room temperature.