Synthetic Approaches for Construction of Novel Angular Heterocyclic Systems Containing Chromeno[2,3-b]quinoline

Abstract

Cyclic β-chloroenaldehyde 1 was used to create a novel series of angular heteroannulated chromones. Condensation of β-chloroenaldehyde 1 with hydrazine derivatives produced chromeno[2,3-b]pyrazolo[3,4-f]quinolines 2, 5 and 6. Also, condensation of compound 1 with some 1,3-N,N-binucleophiles yielded chromeno[2`,3`:6,5]pyrido[2,3-h]quinazolines 7-9. Treating compound 1 with some 1,3-N,C-binucleophiles produced chromeno[2,3-J]phenanthrolines 10, 11, benzoimidazo[1,2-a]chromeno[2,3-J]phenanthroline 12 and chromeno[2,3-J]pyrazolo[3,4-b]phenanthrolines 13, 14. Reacting compound 1 with a diversity of 1The in vitro antimicrobial activity seemed variable inhibitory effect for the prepared compounds.

Synthesis, design, and antimicrobial activity of pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidinones based on quinoline derivatives

“…The 1-phenyl-3-(quinolin-2-yl) prop-2-en-1-one (1) was synthesized through the Claisene-Schmidt reaction, condensation and stirring of quinoline-2-carbaldehyde and acetophenones in ethanol with sodium hydroxide solutions by using the model procedure for the synthesis of chalcones [76]. The IR spectrum of compound (1) demonstrated absorption bands at ν 1750 cm À1 conforming to one carbonyl group. The 1 H-NMR spectrum of (1) exhibited two singlets at δ 8.10, 8.20 ppm corresponding to two methine protons.…”

“…Its IR spectrum of (5a) exhibits the broad bands at ν 3300-3100 cm À1 for the three (3NH) groups and sharp intensity peaks at ν 1672, 1668 cm À1 for the two-carbonyl amide group. 1 H-NMR spectrum of (6a) revealed three singlet signals at δ 7.95, 8.07, and 9.10 ppm for three protons of CH-pyridine and CH-triazole and one proton of…”

“…Most heterocyclic compounds possess many biological and pharmacological activities which are including pyrido [2,3-d]pyrimidine derivatives and which inter in the structure of many drugs because they have many biological and pharmacological activities such as antimicrobial [1][2][3], antioxidant [4][5][6][7], antitubercular [8], antiviral [9], anti-inflammatory [10][11][12], effective glucosidase inhibitor [13,14], adenosine kinase inhibitor [15], a dihydrofolate reductase inhibitor [16,17], and a threonine tyrosine kinase (TTK) inhibitor [18]. In addition, pyrido [2,3-d] [1,2,4]triazolo [4,3-a]pyrimidin-5-ones are pharmacological scaffold that represent a wide range of biological activities such as analgesic, anti-inflammatory, antioxidant, and anti-microbial [19], anti-HCV, anti-SSPE, antimicrobial, antioxidant, and antitumor activities [20], peroxynitrite inhibitory activity, anti-HCV and antioxidant [21], antitumor activity, anti-HCV [22]. As well, the 1, 2, 4-Triazole, 1, 2, 4-triazolopyrimidine, 1, 2, 4-triazolopyrimidofuro-quinazolinone and 1, 2, 4-triazolopyridazine, triazole-spiropyrimidine derivatives showed antimicrobial activity [23][24][25][26][27][28][29].…”

“…In our past work, we prepared a new class of new heterocyclic compounds with the study of the biological activity of these compounds [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75]. Therefore, this work is presented a new style to the synthesis of 2-hydrazinyl-7-phenyl-5-(quinoline)pyrido [2,3-d]pyrimidinone, 3-sub-8-phenyl-6-(quinoline) pyrido [2,3-d] [1,2,4]triazolo [4,3-a] pyrimidinone, and 3-(4-sub-phenyl)-8-phenyl-6-(quinoline)pyrido [2,3-d] [1,2,4]triazolo [4,3-a]pyrimidinone derivatives by using new many of reagents and fast, convenient styles that produce the best yields of new chemical products. T...…”

4-Amino-3-formylcoumarin as Building Block for Construction of Novel Heteroannulated Coumarins: Synthesis, Characterization and Antimicrobial Evaluation

“…Compound 6 has an active methylene ketone moiety, which motivates us to apply Vilsmeier-Haack reaction on this substrate. 25 Thus, the novel 1-chloro-11-oxo-3,4-dihydro-11H-chromeno[3,4-b]quinoline-2-carboxaldehyde (10) was produced by formylation of compound 6 utilizing Vilsmeier Haack reagent (POCl3/DMF) (Scheme 5). In the IR spectrum, characteristic absorption bands were seen at 1718 (C=Oα-pyrone) and 1707 cm -1 (C=Oaldehyde).…”