2021
DOI: 10.1002/slct.202100342
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Synthesis of 3‐Indole Substituted Sulfonyl 4H‐Chromenes Using Recyclable Cyclometrix Polyphosphazene‐Base Catalysts

Abstract: In order to build a library of 3‐indole substituted sulfonyl 4H‐chromenes in green protocol the three‐component one‐pot coupling reactions of substituted salicylaldehydes, sulfonyl acetonitriles and indoles have been performed using recyclable and metal‐free heterogeneous base catalysts. The highly cross‐linked cyclometrix polyphosphazenes (cPOPs) synthesized via a single‐step precipitation polymerization of hexachlorocyclotriphosphazene with 4,4’‐oxydianiline or 3,3’‐diaminobenzidine without using any other a… Show more

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Cited by 9 publications
(6 citation statements)
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“…Currently, salicylaldehyde and its derivatives [23][24][25][26] were widely used in addition-cyclization cascades. The hydroxyl group was acceptors for cyclization.…”
Section: Reactions With Aldehydesmentioning
confidence: 99%
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“…Currently, salicylaldehyde and its derivatives [23][24][25][26] were widely used in addition-cyclization cascades. The hydroxyl group was acceptors for cyclization.…”
Section: Reactions With Aldehydesmentioning
confidence: 99%
“…In our opinion, if the hydroxyl group is replaced by −SH, −N 3 , −COOH, or −NHR, diverse cyclizations will occur. Scheme 17 enumerated reactions of salicylic aldehydes with malonitrile, [23] sulfonyl acetonitriles [24] and 1,3‐dicarbonyls [25] . Panahi [23] achieved malonitrile‐mediated reactions using water as the solvent and LCMP ( L‐ cysteine functionalized magnetic nanoparticles) as the catalyst.…”
Section: Nucleophilic C3mentioning
confidence: 99%
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“…The other important strategies reportedly involved the reaction of phthalaldehydic acid, amine, and indole, the reaction of 2-halo- N -phenylbenzamides, terminal alkyne, and substituted indoles at high temperatures, and cyclization of arylaminophthalides . Salicylaldehyde is a useful building block for the construction of the benzopyran intermediate, which upon metal- or base-catalyzed nucleophilic attack by indole produced indolyl-4 H -chromenes . There are several other important routes for accessing indolyl-4 H -chromene .…”
Section: Introductionmentioning
confidence: 99%
“…However, the synthesis of 4 H ‐chromenes in the presence of catalytically active ionic liquids and M x Sr 2 Nb 2 O 7+δ (M=Cr 3+ , Cu 2+ , Zn 2+ , Ag + , and Cd 2+ ) nanocomposites under microwave and ultrasound irradiations, [12a–c] respectively, has reduced some of the drawbacks. Three recent studies have focused on describing methods for the synthesis of 4 H ‐chromenes in high yields and short reaction times using small amounts of easily prepared heterogeneous catalysts, including amino‐grafted Cu and Sc Metal‐Organic Frameworks (MOFs), [12d] immobilized piperazine on the surface of graphene oxide (GO), [12e] and cyclometrix polyphosphazenes (cPOPs) [12f] . Thus, the development of sustainable, low‐cost, and efficient heterogeneous catalysts to synthesize 4 H ‐chromenes using non‐traditional heating methods is still of great interest in organic synthesis and drug discovery.…”
Section: Introductionmentioning
confidence: 99%