2015
DOI: 10.1002/jhet.2503
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A Facile Three‐Component One‐Pot Synthesis of Some Novel Tricyclic Hetero‐Ring Systems

Abstract: A novel, facile, one‐pot, multicomponent reaction for the synthesis of a series of pyrano[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine and pyrano[2′,3′:4,5]pyrimido[2,1‐b][1,3,5]thiadiazine derivatives has been developed from reaction of 2,4‐dichlorobezaldehyde, malononitrile, and the appropriate active methylene compounds in refluxing dioxane in the presence of chitosan. A plausible mechanism has been proposed for this reaction, and the structure of the newly synthesized compounds was all established on the basis o… Show more

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Cited by 11 publications
(5 citation statements)
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“…[18][19][20][21] Multicomponent reactions (MCR) are one-pot processes which always occupy great importance in the repertoire of sustainable synthetic tools because of their high efficiency and atom economy. 22,23 As part of our ongoing studies on the synthesis of new heterocyclic compounds via one-pot, multicomponent reactions, [24][25][26][27][28][29][30][31][32][33] herein this study describes a convenient and rapid method for the synthesis of thiazolyl-hydrazono-ethylthiazole derivatives by one-pot three-component reactions using 2-(2-benzylidenehydrazinyl)-4-methylthiazole (1), thiosemicarbazide (2) and the appropriate hydrazonoyl chlorides (3a-e or 7a-d) or phenacyl bromides (10a-e) in the presence of a catalytic amount of TEA in dioxane. The cytotoxic potential of the newly synthesized compounds was examined against HCT-116, HT-29 and HepG2 cells using the MTT assay to elucidate its underlying mechanisms of action related to their anti-apoptotic BCl2 family proteins.…”
Section: Introductionmentioning
confidence: 99%
“…[18][19][20][21] Multicomponent reactions (MCR) are one-pot processes which always occupy great importance in the repertoire of sustainable synthetic tools because of their high efficiency and atom economy. 22,23 As part of our ongoing studies on the synthesis of new heterocyclic compounds via one-pot, multicomponent reactions, [24][25][26][27][28][29][30][31][32][33] herein this study describes a convenient and rapid method for the synthesis of thiazolyl-hydrazono-ethylthiazole derivatives by one-pot three-component reactions using 2-(2-benzylidenehydrazinyl)-4-methylthiazole (1), thiosemicarbazide (2) and the appropriate hydrazonoyl chlorides (3a-e or 7a-d) or phenacyl bromides (10a-e) in the presence of a catalytic amount of TEA in dioxane. The cytotoxic potential of the newly synthesized compounds was examined against HCT-116, HT-29 and HepG2 cells using the MTT assay to elucidate its underlying mechanisms of action related to their anti-apoptotic BCl2 family proteins.…”
Section: Introductionmentioning
confidence: 99%
“…In these last two decades, we have launched a program designed to create new easy, synthetic paths to heterocyclic systems that are functionally replaced, using inexpensive laboratory materials with anticipated bioactivities . Under our program, some new pyridine‐fused aza heterocyclic compounds have to be evaluated for biological activity.…”
Section: Introductionmentioning
confidence: 99%
“…[29][30][31] In these last two decades, we have launched a program designed to create new easy, synthetic paths to heterocyclic systems that are functionally replaced, using inexpensive laboratory materials with anticipated bioactivities. [32][33][34][35][36][37][38][39][40][41][42] Under our program, some new pyridine-fused aza heterocyclic compounds have to be evaluated for biological activity. It was expected that combining a triazole ring with a pyridine and/or a pyrimidine ring in one system could lead to improved biological activity.…”
Section: Introductionmentioning
confidence: 99%
“…In the past few decades, we were involved in a program aiming at the synthesis of heterocyclic compounds of expected biological activity [6][7][8][9][10][11][12][13][14][15]. In the context of this trend and, because of the striking biological activities of tetracycline derivatives, we report here simple syntheses of some new heterocyclic pentacycline derivatives as a novel class of tetracycline analogs starting from indane-1,3-dione.…”
Section: Introductionmentioning
confidence: 99%