MNPs‐NHC6H4SO3H as high‐performance catalyst for the synthesis of 1,4‐diazepines containing tetrazole ring under microwave irradiation

Safaei‐Ghomi, Javad; Paymard-Samani, Soleiman; Shahbazi‐Alavi, Hossein

doi:10.1002/jccs.201700349

Cited by 4 publications

(3 citation statements)

References 32 publications

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“…In this reaction cyclic imine is in situ generated and consumed (Scheme ). In addition, these tetrazole heterocyclic compounds were synthesized using the MNPs-NHC 6 H 4 SO 3 H and MCM-48/H 5 PW 10 V 2 O 40 catalysts. ,, …”

Section: Cyclic Imines In Azido−ugi Reactionsmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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Ugi four-component reactions (U-4CRs) are widely recognized as being highly efficient for the synthesis of pseudopeptides. However, the products of these reactions are not so interesting as drug candidates because they are not conformationally restricted enough for a potent interaction with biological targets. One possible way to overcome this problem is to replace amine and oxo components in the U-4CRs with cyclic imines in so-called Joullié−Ugi three-component reactions (JU-3CRs). This approach provides a robust single-step route to peptide moieties connected to N-heterocyclic motifs that are found as core skeletons in many natural products and pharmaceutical compounds. JU-3CRs also provide much better diastereoselectivity than their four-component analogues. We survey here the redesign of many synthetic routes for the efficient preparation of a wide variety of three-, five-, six-, and seven-membered heterocyclic compounds connected to the peptide backbone. Additionally, in the Ugi reactions based on the cyclic imines, α-acidic isocyanides, or azides can be replaced with normal isocyanides or acids, respectively, leading to the synthesis of N-heterocycles attached to oxazoles or tetrazoles, which are of great pharmaceutical significance. This Review includes all research articles related to Ugi reactions based on the cyclic imines to the year 2020 and will be useful to chemists in designing novel synthetic routes for the synthesis of individual and combinatorial libraries of natural products and drug-like compounds.

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Section: Cyclic Imines In Azido−ugi Reactionsmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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“…Quinolines are specic heterocyclic pharmacophores with diverse medicinal chemistry and several interesting pharmacological and therapeutic characteristics. [37][38][39] They are also used as the core moieties to prepare many well-known drugs with antifungal, antioxidant, and antituberculous activity (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

CuI nanoparticle-immobilized on a hybrid material composed of IRMOF-3 and a sulfonamide-based porous organic polymer as an efficient nanocatalyst for one-pot synthesis of 2,4-diaryl-quinolines

2023

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“…Elemental analysis results showed that the content of nickel, aluminum, and oxygen in the NiAl 2 O 4 spinel nanocrystals was 48.56, 15.13, 36.31 (wt%), respectively. As a result of our great interest in preparation of heterocyclic compounds by applying heterogeneous catalysts, [26,27] herein we wish to report an efficient procedure to synthesize 2,3-dihydroquinazolin-4(1H)-one derivatives through a threecomponent one-pot condensation of isatoic anhydride, aromatic aldehyde, and primary amines/ or ammonium acetate using NiAl 2 O 4 spinel nanocrystals as catalysts under microwave irradiation (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

A three‐component process for the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐one derivatives using nanosized nickel aluminate spinel crystals as highly efficient catalysts

Safaei‐Ghomi

Teymuri

2019

J Chinese Chemical Soc

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NiAl2O4 spinel nanocrystals were synthesized as mesoporous catalysts and were fully characterized using Fourier‐transform infrared spectroscopy (FT‐IR), X‐ray diffraction patterns (XRD), scanning electron microscopy (SEM), and Energy‐dispersive X‐ray spectroscopy (EDS). These nanocrystals catalyzed the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐one derivatives via a one‐pot, three‐component condensation reaction of aromatic aldehydes, isatoic anhydride, and ammonium acetate or primary aromatic amine under microwave irradiation. By far, the most obvious advantages of the offered process are efficiency and recyclability of the catalyst as well as a significantly shorter reaction time.

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MNPs‐NHC₆H₄SO₃H as high‐performance catalyst for the synthesis of 1,4‐diazepines containing tetrazole ring under microwave irradiation

Cited by 4 publications

References 32 publications

Cyclic Imines in Ugi and Ugi-Type Reactions

Cyclic Imines in Ugi and Ugi-Type Reactions

CuI nanoparticle-immobilized on a hybrid material composed of IRMOF-3 and a sulfonamide-based porous organic polymer as an efficient nanocatalyst for one-pot synthesis of 2,4-diaryl-quinolines

A three‐component process for the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐one derivatives using nanosized nickel aluminate spinel crystals as highly efficient catalysts

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