Catalyst-free domino-Knoevenagel-hetero-Diels–Alder reaction of terminal alkynes in water: an efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives

Majumdar, K. C.; Taher, Abu; Ponra, Sudipta

doi:10.1016/j.tetlet.2009.10.108

Cited by 29 publications

(10 citation statements)

References 54 publications

(24 reference statements)

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“…Ananikov and coworkers disclosed a three-step synthesis of polycyclic compound 116 from bio-based 5-(hydroxymethyl)furfural (HMF) (113) involving a Diels-Alder cycloaddition step (Scheme 27) [99]. Computational calculations demonstrated that the Diels-Alder reaction of 2,5-bis(hydroxymethyl)furan (BHMF) (114) and maleimide is energetically more favorable than that of HMF (113) with the same dienophile. Thus, HMF (113) was reduced to BHMF (114) in aqueous solution.…”

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

“…Computational calculations demonstrated that the Diels-Alder reaction of 2,5-bis(hydroxymethyl)furan (BHMF) (114) and maleimide is energetically more favorable than that of HMF (113) with the same dienophile. Thus, HMF (113) was reduced to BHMF (114) in aqueous solution. Subsequent cycloaddition reaction of 114 with maleimide (55d) in water furnished compound 115 diastereoselectively (96% de) as the endo-adduct in 67% yield.…”

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

“…To prevent the retro-Diels-Alder transformation, 115 was further reduced, giving compound 116 in 87% yield (58% overall yield). It is noteworthy that the three-step one-pot protocol in water, starting from HMF (113), proved to be more efficient, allowing the synthesis of 116 in 73% yield. Ananikov and coworkers disclosed a three-step synthesis of polycyclic compound 116 from bio-based 5-(hydroxymethyl)furfural (HMF) (113) involving a Diels-Alder cycloaddition step (Scheme 27) [99].…”

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

“…It is noteworthy that the three-step one-pot protocol in water, starting from HMF (113), proved to be more efficient, allowing the synthesis of 116 in 73% yield. Ananikov and coworkers disclosed a three-step synthesis of polycyclic compound 116 from bio-based 5-(hydroxymethyl)furfural (HMF) (113) involving a Diels-Alder cycloaddition step (Scheme 27) [99]. Computational calculations demonstrated that the Diels-Alder reaction of 2,5-bis(hydroxymethyl)furan (BHMF) (114) and maleimide is energetically more favorable than that of HMF (113) with the same dienophile.…”

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

“…To prevent the retro-Diels-Alder transformation, 115 was further reduced, giving compound 116 in 87% yield (58% overall yield). It is noteworthy that the three-step one-pot protocol in water, starting from HMF (113), proved to be more efficient, allowing the synthesis of 116 in 73% yield. Recently, the Bruijnincx group disclosed the Diels-Alder reaction of furfurals with water-soluble maleimides in aqueous medium [100].…”

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

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Diels–Alder Cycloaddition Reactions in Sustainable Media

2022

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Diels–Alder cycloaddition reaction is one of the most powerful strategies for the construction of six-membered carbocyclic and heterocyclic systems, in most cases with high regio- and stereoselectivity. In this review, an insight into the most relevant advances on sustainable Diels–Alder reactions since 2010 is provided. Various environmentally benign solvent systems are discussed, namely bio-based derived solvents (such as glycerol and gluconic acid), polyethylene glycol, deep eutectic solvents, supercritical carbon dioxide, water and water-based aqueous systems. Issues such as method’s scope, efficiency, selectivity and reaction mechanism, as well as sustainability, advantages and limitations of these reaction media, are addressed.

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Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

“…To prevent the retro-Diels-Alder transformation, 115 was further reduced, giving compound 116 in 87% yield (58% overall yield). It is noteworthy that the three-step one-pot protocol in water, starting from HMF (113), proved to be more efficient, allowing the synthesis of 116 in 73% yield. Recently, the Bruijnincx group disclosed the Diels-Alder reaction of furfurals with water-soluble maleimides in aqueous medium [100].…”

Section: Noncatalyzed Diels-alder Cycloaddition Reactionsmentioning

confidence: 99%

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