Synthesizing Substituted 2-Amino-2-chromenes Catalyzed by Tertiaryamine-Functionalized Polyacrylonitrile Fiber for Students To Investigate Multicomponent Reactions and Heterogeneous Catalysis

Abstract

A multistep experiment for a synthesis laboratory course that incorporates topics in organic synthesis, chemical analysis, and instrumental analysis was developed. Students prepared a tertiaryamine-functionalized polyacrylonitrile fiber (PAN T F), and it was subsequently utilized as an immobilized catalyst in a threecomponent condensation reaction among an aromatic aldehyde, malononitrile, and αnaphthol in ethanol to synthesize substituted 2-amino-2-chromenes in one pot. The fiber catalyst exhibits the advantages of high yield, excellent recyclability and reusability, simple post-treatment, and environmental friendliness. Thus, students were able to apply the concept of green chemistry through catalysis. Moreover, this comprehensive experiment involves a number of unit operations, such as vacuum distillation, filtration, recrystallization, and acid−base titration, which can train the fundamental operation capability of students, and improve their experimental skills.

Synthesis and Characterization of H5PV2Mo10O40@Cu3(BTC)2 and Its Use as a Heterogeneous Catalyst for Oxidative Desulfurization: A Comprehensive Chemistry Laboratory Experiment

“…2 Tao et al presented an educational experiment for advanced organic chemistry students, in which students prepared a tertiaryamine-functionalized polyacrylonitrile fiber and utilized it as heterogeneous catalyst to synthesize substituted 2-amino-2-chromenes. 3 Ulkowska et al developed a laboratory experiment, which included the synthesis of a heterogeneous copper catalyst and its application in the dehydrogenation of cyclohexanol performed under flow conditions. 4 The sulfur compounds in fuels can convert into SOx when fuel oils are burning and subsequently cause the formation of smog, PM 2.5, and acid rain.…”

“…For example, Anastas et al described a laboratory experiment that illustrated several principles of green chemistry through a simple oxidative cleavage reaction using a heterogeneous metal oxide catalyst . Tao et al presented an educational experiment for advanced organic chemistry students, in which students prepared a tertiaryamine-functionalized polyacrylonitrile fiber and utilized it as heterogeneous catalyst to synthesize substituted 2-amino-2-chromenes . Ulkowska et al developed a laboratory experiment, which included the synthesis of a heterogeneous copper catalyst and its application in the dehydrogenation of cyclohexanol performed under flow conditions …”

A Comprehensive Inquiry-Based Comparative Experiment for an Undergraduate Organic Chemistry Laboratory Course: Elucidating the Formation Process of N-Phenylbenzamide

“…The results of comparative experiments between reactions 1 and 2 in Scheme 3 provide evidence that the product formation was from the breaking of the C�N double bond within N-benzylideneaniline. The results from control 2 show that aniline can react with bis(4-methylbenzoyl) peroxide to yield 4-methyl-N-phenylbenzamide (5). Therefore, it can be concluded that aniline as an intermediate can react with benzoyl peroxide to give N-phenylbenzamide (2).…”

Research Progress of Functional Polyacrylonitrile Fiber in Promoting Organic Reaction

“…该催化剂可用于催化多种 芳香醛反应, 并以 80%～99%的收率得到产物, 并且催 化剂可循环使用 7 次. 他们还报道 [108] 了一种简单的叔 胺功能化的纤维催化剂 PAN T F (48), 并将其用于合成取 代 2-氨基-2-色烯的反应, 以 86%～97%的收率合成了几 种不同的取代产物.…”