One-pot synthesis of 4-alkyl-2-amino-4H-chromene derivatives

Abstract

A one-pot synthesis of 4-alkyl-2-amino-4H-chromene derivatives by base-initiated reactions of aliphatic aldehydes, malononitrile, and resorcinol in water is described.

Novel aminochromone derivative inhibits tumor growth on xenograft model of lung cancer in mice

“…one-pot method in N-acetylamino-ethanoate form. [9] The substance was administered intragastrically daily at 50 mg/kg dose, which was 1% of the LD 50 value determined for this route of administration, in 0.5 ml of 2% starch gel, 7 days after tumor transplantation for 7 days as an effective regimen on in vivo syngeneic model of Lewis lung carcinoma in mice. [10] AX-544 starch formulation was prepared ex tempore .…”

First Synthesis of 2-Amino-5-hydroxy-4H-chromene-3-carbonitriles from 4-(2-Pyridylazo)resorcinol

“…Interest in chromenes 1 is also due to their preparative availability: these compounds are easily obtained from activated phenols, carbonyl compounds, and malononitrile under a widely varied range of conditions (Scheme 1). Resorcinol and some of its derivatives are often used as activated phenols [7][8][9][10][11][12]. Over the past 5 years, a number of works have appeared [13][14][15][16] describing the preparation of 6-(arylazo)-2amino-4H-chromenes 2 from 4-(arylazo)resorcinols 3.…”

“…The base required for the Knoevenagel condensation between aldehydes and malononitrile and subsequent Michael addition to arylidenemalononitriles 6 is sodium acetate, which is formed in situ after the addition of acetic acid. FIRST SYNTHESIS OF 2-AMINO-5-HYDROXY-4H-CHROMENE-3-CARBONITRILES It should be specially noted that, in the case of unsubstituted resorcinol [7][8][9][10][11][12] and 4-(arylazo)resorcinols [13][14][15][16], the condensation products are 7-OHchromenes, while in the case of PAR, 5-OH isomers 5 are formed. 5-Hydroxy-4Н-chromenes have been previously observed in the case of orcin (5-methylresorcinol) [40,41] or resorcinols having a strong acceptor substituent in position 4 [42][43][44].…”

One‐pot synthesis of new functionalized 4H‐chromen‐4‐ylidene derivatives

“…These structures are used as biological agents and pharmaceutical applications [24,25]. They include anti‐helminthic [26], antibacterial, fungicidal [27], anticancer [28,29] antitumor, antiallergic [30], antimicrobial, antiviral [31–33] spasmolytic [34,35], anti‐HIV [36], and anti‐depressant [37] properties. Some naturally occurring chromenes that possess biological activities [38] are shown in Figure 1.…”