Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives

Abstract

Herein, we report a non‐metal strategy for cyclization reactions of 2‐vinylanilines with/without isonitriles to synthesize 2‐aminoquinoline and 3‐aryl‐1H‐indole derivatives. A series of 2‐aminoquinolines were afforded in good to excellent yields in a direct, facile, and efficient approach by Se‐catalyzed isocyanide insertion with 2‐vinylanilines under an air atmosphere. This reaction not only used low toxicity Se as the catalyst, isocyanobenzene substrates were compatible too compared to previous report. Meanwhile, an intramolecular cyclization of 2‐vinylanilines was developed to give 3‐aryl‐1H‐indoles in moderate to good yields by using SeO2 as oxidant.

Diversification Via Coupling Reactions and Biological Activities of Pyrimidine Derivatives

“…The interactions of pyrimidine derivatives with biological targets, such as enzymes, receptors, and signaling cascades, are significantly influenced by the structural alterations produced by coupling processes. [10,[46][47][48] Diversified pyrimidine derivatives have shown strong anticancer effects in oncology by targeting cancer cells, blocking important enzymes involved in nucleotide metabolism, and interfering with DNA replication and repair processes. The review will emphasize the connections between these derivatives' chemical structures and functions and the mechanisms underlying their capabilities, emphasizing their potential as potent chemotherapeutic agents.…”

“…The pyrimidine ring system can be altered, or functional groups added to it to create compounds with various pharmacological properties. [4][5][6][7] Pyrimidine is a major N-heterocyclic compound because it is an essential component of many important biological molecules. As pyrimidines are ubiquitous in living systems, modified pyrimidine derivatives were among the first heterocyclic substances studied by organic chemists.…”

“…Numerous medications, including well‐known classes like anticancer medications (5‐fluorouracil), antiviral drugs (acyclovir), and diuretics (hydrochlorothiazide), are based on heterocyclic structures. The pyrimidine ring system can be altered, or functional groups added to it to create compounds with various pharmacological properties [4–7] …”

Gold‐Catalyzed Annulation of Ynamides with Aminocarbonyls as a Route to 2‐Aminoquinolines Diversely Substituted at the 4th‐Position

“…[13,14] It is not surprising, therefore, that preparative approaches to construct 2-aminoquinolines are in high demand, and a number of impressive synthetic reports on this topic have recently been published. [15][16][17][18][19][20][21][22] In this study, we developed a modular and practical approach to 2-aminoquinolines, which is based on annulation of ynamides. Ynamides, i. e. amido-functionalized alkynes [23,24] have been commonly recognized as easily available and handy building blocks for a facile construction of complex molecules, [24][25][26][27] including diverse carbo-and heterocycles.…”

“…Furthermore, 2‐aminoquinolines are currently studied as antidepressants (quipazine [10] and its 4‐derivatives [11] ) or drugs against Sickle cell disease [12] and certain cancers [13,14] . It is not surprising, therefore, that preparative approaches to construct 2‐aminoquinolines are in high demand, and a number of impressive synthetic reports on this topic have recently been published [15–22] …”