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. 2024 Jul 16;14(30):21608-21622.
doi: 10.1039/d4ra04239e. eCollection 2024 Jul 5.

A facile one-pot synthesis of tetrahydrobenzo[ b]pyrans and 2-amino-4 H-chromenes under green conditions

Sarieh Momeni  1 , Ramin Ghorbani-Vaghei  1
Affiliations

A facile one-pot synthesis of tetrahydrobenzo[ b]pyrans and 2-amino-4 H-chromenes under green conditions

Sarieh Momeni et al. RSC Adv. .

Abstract

This research developed a new nanocatalyst by incorporating nanocopper iodide onto the surface of a layered double hydroxides modified. This new nanocatalyst enables the green synthesis of tetrahydrobenzo[b]pyrans and 2-amino-4H-chromene derivatives through a one-pot, three-component reaction, demonstrating remarkable activity and selectivity. Key advantages of this method include increased products yield (86-96%), rapid reaction kinetics (5-23 minutes), low reaction temperature (40 °C), synthesis of new products, straightforward purification methods, catalyst recyclability (up to 4 cycles), and solvent-free conditions.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Scheme 1
Scheme 1. The steps of catalytic LDH@PTRMS@NDBD@CuI synthesis.
Fig. 1
Fig. 1. FTIR spectra of (a) double hydroxide layer, (b) LDH@PTRMS, (c) melamine (d) NDBD ligand, (e) LDH@PTRMS@NDBD and (f) LDH@PTRMS@NDBD@CuI.
Fig. 2
Fig. 2. EDX analysis of LDH@PTRMS@NDBD@CuI catalyst.
Fig. 3
Fig. 3. Elemental mapping analysis (MAPPING) of LDH@PTRMS@NDBD@CuI catalyst.
Fig. 4
Fig. 4. FESEM images of Zn/Cr-LDH@PTRMS@NDBD@CuI catalyst.
Fig. 5
Fig. 5. X-ray diffraction of the catalyst and its intermediates (a) double hydroxide layer, (b) LDH@PTRMS, (c) LDH@PTRMS@NDBD and (d) LDH@PTRMS@NDBD@CuI.
Fig. 6
Fig. 6. TGA and DSC thermal analyzes of Zn/Cr-LDH@PTRMS@NDBD@CuI catalyst.
Fig. 7
Fig. 7. Exploring substitution groups in the synthesis of tetrahydrobenzo[b]pyrans via the Hammett plot.
Scheme 2
Scheme 2. Proposed mechanism for the synthesis of tetrahydrobenzo[b]pyran derivatives in the vicinity of Zn/Cr-LDH@PTRMS@NDBD@CuI catalyst.
Scheme 3
Scheme 3. Proposed mechanism of synthesis of 2-amino-4H-chromenes derivatives in the vicinity of Zn/Cr-LDH@PTRMS@NDBD@CuI catalyst.
Fig. 8
Fig. 8. Ability to recycle and reuse Zn/Cr-LDH@PTRMS@NDBD@CuI catalyst.
See this image and copyright information in PMC

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