Adipic Acid as a Biodegradable Solid Acid Catalyst for One-Pot, Three Component Synthesis of 1-Amidoalkyl-2-naphthols

Abstract

Background: 1-Amidoalkyl-2-naphthols are an attractive group of organic compounds that can be converted to oxazine heterocycles and aminoalkyl naphthols. The derivatives of 1- amidoalkyl-2-naphthols have significant biological activities and act as drug candidates. Methods: 1-Amidoalkyl-2-naphthols were synthesized via the three-component condensation reaction of 2-naphthol, acetamide/benzamide and various aldehydes in the presence of 10 mol% of adipic acid as an organocatalyst under solvent-free conditions at 120°C. Results: A simple, efficient, and operative method for the synthesis of 1-amidoalkyl-2-naphtholes in the presence of adipic acid as the biodegradable catalyst is introduced. Easy operation, acceptable reaction times, eco-friendly, availability of starting materials, simple separation of products, and high yields of products are the significant results of this method. Conclusion: In this study, 1-amidoalkyl-2-naphthols were synthesized using commercially available reactants in excellent yields and relatively shorter times. In this process, microwave or ultrasonic waves were not used to provide energy for the reaction.

Recent Advances in the Reactions of β-Naphthol at α-Position

“…同样的, Ghorbani-Choghamarani 课题组 [33] 和巩凯课 题组 [34] 也分别相继使用三聚氰胺-Br 3 和 β-环糊精-丁烷 磺酸等催化剂完成了该反应, 顺利构建 1-酰胺烷基-2-萘酚及其衍生物. 2020 年 Kiyani 课题组 [35] 报道了己二酸 作为催化剂也能高效地催化该反应的进行, 与其它类型 的催化剂相比, 己二酸具有绿色、反应时间短及收率高 的优点, 且无需其它条件如微波或超声波等辅助催化.…”

Amidoalkyl Naphthols as Important Bioactive Substances and Building Blocks: A Review on the Current Catalytic Mannich-Type Synthetic Approaches

“…The synthesis of 19 amidoalkyl naphthols was achieved in 60-92% yields in the range of 1-7 h [23]. Darbandi et al, made use of 10 mol% adipic acid as a catalyst in a similar three-component condensation of 2-naphthol under solvent-free conditions and 120 • C. Yields of up to 96% for 21 amidoalkyl naphthols have been achieved in shorter reaction times that lay in the range of 9 to 76 min [60]. Another efficient solvent-free method was reported by Sadeghi and Moradi.…”

Solvent free synthesis of amidoalkyl derivatives under green and convenient conditions

“…Amido alkyl derivatives have been synthesis with different homogeneous and heterogeneous catalysts like acidic catalysts [5,11–30], magnetic catalysts [31–33], ionic liquid [34–36], and metallic nanoparticles [37–41]. Some of them have disadvantages like long reaction times, low product yields, using of hazardous solvents, synthesis of catalysts in several stages, and use of expensive materials to the synthesis of catalysts.…”

“…It should be noted that amidomethyl β-naphtholes could be converted to important biological and pharmacological derivatives of by the hydrolysis reaction of amide. Amido alkyl derivatives have been synthesis with different homogeneous and heterogeneous catalysts like acidic catalysts [5,[11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30], magnetic catalysts [31][32][33], ionic liquid [34][35][36], and metallic nanoparticles [37][38][39][40][41]. Some of them have disadvantages like long reaction times, low product yields, using of hazardous solvents, synthesis of catalysts in several stages, and use of expensive materials to the synthesis of catalysts.…”