Abstract
A one-pot three component reaction of benzaldehydes, 1H-tetrazole-5-amine, and 3-cyanoacetyl indole in the presence of a new hexamethylenetetramine-based ionic liquid/MIL-101(Cr) metal–organic framework as a recyclable catalyst was explored. This novel catalyst, which was fully characterized by XRD, FE-SEM, EDX, FT-IR, TGA, BET, and TEM exhibited outstanding catalytic activity for the preparation of a range of pharmaceutically important tetrazolo[1,5-a]pyrimidine-6-carbonitriles with good to excellent yields in short reaction time.
Highlights
Fused heterocycles are a unique family of conjugated structures widely identified as core units in drug discovery[1,2]
HMTA-BAIL ionic liquid was incorporated into the MIL‐101(Cr) Metal organic frameworks (MOFs) pores to construct a novel ionic liquids (ILs)/MOF hybrid composite, denoted as HMTA-BAIL@ MIL-101(Cr)
The structure of the resultant new nanoporous material was investigated by several techniques such as powder X-ray diffraction patterns (PXRD), field emission scanning electron microscopy (FE-SEM), energydispersive X-ray (EDX), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), The N2 adsorption–desorption isotherm (BET) and transmission electron microscopy (TEM)
Summary
Fused heterocycles are a unique family of conjugated structures widely identified as core units in drug discovery[1,2]. The construction of a triazolopyrimidine unit with an incorporated indole nucleus could offer unique skeletons, named as tetrazolo[1,5-a]pyrimidine-6-carbonitriles, with outstanding biological activities such as antiproliferative and antitumor e ffects[12,13] The exploitation of these privileged structures with the ability of binding to multiple receptors could allow medicinal chemists to quickly uncover many bioactive scaffolds across a wide range of therapeutics. Despite this significance, there are only quite a few synthetic methods for the preparation of these target candidates[12,13], in which they suffer from several drawbacks such as high temperature, long reaction time, hazardous organic solvent, and the use of stoichiometric amount of toxic triethylamine as catalyst. It has been shown that the incorporation of ILs into the highly porous materials such as MOFs could overcome this d isadvantages[25]
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