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Extended Abstract

Microwave Accelerates the Synthesis of 1-Amidoalkyl-2-Naphthols Using Cu2(NH2-BDC)2(DABCO)-Sal-Co(II) as a Heterogeneous Catalyst †

by
Leila Panahi
and
M. Reza Naimi-Jamal
*
Research Laboratory of Green Organic Synthesis & Polymers, Department of Chemistry, Iran University of Science and Technology, P.O. Box 16846-13114 Tehran, Iran
*
Author to whom correspondence should be addressed.
†
Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November– 15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22.
Proceedings 2019, 9(1), 68; https://doi.org/10.3390/ecsoc-22-05698
Published: 14 November 2018
(This article belongs to the Proceedings of 22nd International Electronic Conference on Synthetic Organic Chemistry)
Browse Figure
Versions Notes
Multicomponent reactions have attracted significant attention since they are performed without the need to isolate any intermediate during their process; this diminishes the time and saves both energy and raw materials [1,2]. Derivatives of 1-Amidoalkyl-2-naphthol are of importance, as they can be easily converted to biologically active compounds through amide hydrolysis reaction [3]. Recently, various catalysts have been used to prepare these compounds through a multicomponent reaction. In this research, metal–organic frameworks (MOFs) were utilized as heterogeneous catalysts. They are often crystalline solids consisting of metal ions or clusters coordinated to mostly rigid organic linkers such as aromatic polycarboxylates or polyamines to form one-, two-, or three-dimensional porous structures [4]. We report a green and convenient method for the synthesis of 1-amidoalkyl-2-naphthols from the reaction between β-naphthol, aromatic aldehydes, and amide derivatives under microwave irradiation in the presence of Cu2(NH2-BDC)2(DABCO)-Sal-Co(II) as a modified catalyst through a post-synthesis method. (Scheme 1).
Cu2(NH2-BDC)2(DABCO) was synthesized and then modified with salicylaldehyde and cobalt acetate (II) salt by the ball-milling technique.

References

  1. Devi, I.; Bhuyan, P.J. Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions. Tetrahedron Lett. 2004, 45, 8625. [Google Scholar] [CrossRef]
  2. Mashraqui, S.H.; Patil, M.B.; Mistry, H.D. A Three-component Reaction of Phenol, Aldehyde, and Active Methylene Substrate under Lewis acid Catalysis: Successful Trapping of o-Quinone Methide to Afford Benzopyran Systems. Ghadigaonkar, S.; Meetsma, A. Chem. Lett. 2004, 33, 1058. [Google Scholar] [CrossRef]
  3. Shen, A.Y.; Chen, C.L.; Lin, C.C. Electrophysiological basis for the bradycardic effects of 1-(1-pyrrolidinylmethyl)-2-naphthol in rodents. J. Physiol. 1992, 35, 45. [Google Scholar]
  4. Cook, T.R.; Zheng, Y.R.; Stang, P.J. Metal–Organic Frameworks and Self-Assembled Supramolecular Coordination Complexes: Comparing and Contrasting the Design, Synthesis, and Functionality of Metal–Organic Materials. Chem. Rev. 2013, 113, 734–777. [Google Scholar] [CrossRef] [PubMed]
Proceedings 09 00068 sch001
Scheme 1. Synthesis of 1-Amidoalkyl-2-naphthol derivatives catalyzed by metal–organic frameworks (MOFs).
Scheme 1. Synthesis of 1-Amidoalkyl-2-naphthol derivatives catalyzed by metal–organic frameworks (MOFs).
Proceedings 09 00068 sch001
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MDPI and ACS Style

Panahi, L.; Naimi-Jamal, M.R. Microwave Accelerates the Synthesis of 1-Amidoalkyl-2-Naphthols Using Cu2(NH2-BDC)2(DABCO)-Sal-Co(II) as a Heterogeneous Catalyst. Proceedings 2019, 9, 68. https://doi.org/10.3390/ecsoc-22-05698

AMA Style

Panahi L, Naimi-Jamal MR. Microwave Accelerates the Synthesis of 1-Amidoalkyl-2-Naphthols Using Cu2(NH2-BDC)2(DABCO)-Sal-Co(II) as a Heterogeneous Catalyst. Proceedings. 2019; 9(1):68. https://doi.org/10.3390/ecsoc-22-05698

Chicago/Turabian Style

Panahi, Leila, and M. Reza Naimi-Jamal. 2019. "Microwave Accelerates the Synthesis of 1-Amidoalkyl-2-Naphthols Using Cu2(NH2-BDC)2(DABCO)-Sal-Co(II) as a Heterogeneous Catalyst" Proceedings 9, no. 1: 68. https://doi.org/10.3390/ecsoc-22-05698

APA Style

Panahi, L., & Naimi-Jamal, M. R. (2019). Microwave Accelerates the Synthesis of 1-Amidoalkyl-2-Naphthols Using Cu2(NH2-BDC)2(DABCO)-Sal-Co(II) as a Heterogeneous Catalyst. Proceedings, 9(1), 68. https://doi.org/10.3390/ecsoc-22-05698

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