Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences

Ghandi, Mehdi; Bozcheloei, Abolfazl Hasani; Nazari, S. Hadi; Sadeghzadeh, Masoud

doi:10.1021/jo201506d

Cited by 20 publications

(5 citation statements)

References 70 publications

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“…Their paper [38] provide an easy-performed one-pot interaction of the substituted 2-hydroxybenzaldehydes 38 with the 4-substituted 2-phenylethenesulfonyl chlorides 39 in DMF in the presence of DBU that led to the formation of benzylbenzo[e] [1,2]oxathiin-4(3H)-one 2,2-dioxides 41 (Scheme 12). Scientists also managed to isolate the intermediates -2-formylphenyl-2-phenylethnesulfonates 40 and to investigate the effect of the solvent on the cyclization process.…”

Section: Resultsmentioning

confidence: 99%

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Hryhoriv

Lega

Shemchuk

2021

J. org. pharm. chem.

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Aim. To analyze the available literature data on the methods of synthesis, chemical transformations and the biological activity of derivatives containing a sultone core – 1,2-benzoxathiin-4(3H)-one 2,2-dioxide – and to show the possibilities of their further use in the construction of new molecular systems with attractive pharmacological properties. Results and discussion. The most widespread method for the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides is the cyclization of salicylic acid derivatives. The known chemical transformations of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides deal with all reaction centers of the heterocyclic fragment of the condensed system – C=O and CH2 groups, SO2–O bond, CH2CO fragment as a whole. It should be noted that the oxathiine nucleus is prone to undergo recyclizations. The use of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides in multicomponent transformations still remains hardly explored. The “abnormal” course of some classical transformations involving 1,2-benzoxathiine 2,2-dioxides is also noteworthy. The study of the pharmacological properties of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide derivatives is scarce and mainly based on their structural similarity to the coumarin core, which led to the study of anticoagulant, antimicrobial and antitumor properties for the sultone derivatives. Conclusions. The analysis has shown a limited number of studies in each aspect – approaches to the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides, their chemical transformations and the study of their pharmacological activity. In addition to a small number of publications on this heterocyclic system, there have been almost no sultone studies in the last 20 years. Taking this into account 1,2-benzoxathiin-4(3H)-one 2,2-dioxide and its derivatives deserve close attention as objects of research for experimental chemistry and pharmacology.

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Section: Resultsmentioning

confidence: 99%

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Hryhoriv

Lega

Shemchuk

2021

J. org. pharm. chem.

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“…To demonstrate the synthetic utility of our method, a sequential reaction strategy has been designed for the synthesis of benzo‐δ‐sultone. In this regard, 2‐formylphenyl‐( E )‐2‐phenylethenesulfonate 3am ,a reactive intermediate was synthesized using our optimized reaction conditions, which was further transformed to benzo‐δ‐sultone 5 a via DBU‐catalyzed intramolecular Baylis‐Hillman reaction (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

2‐Formylarylsulfonate from Aryne: A Sequential Reaction Strategy for Direct Synthesis of ortho‐Hydroxyl‐Protected Aryl Aldehydes

Sharma

Gogoi

2017

ChemistrySelect

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A novel transition‐metal free synthetic strategy has been developed for the direct synthesis of 2‐formylarylsulphonate from aryne precursor. The reaction proceeds via CO and C−C bond cleavage as well as C−O,C−C and O−S bond formations in a single reaction vessel. The methodology provides good yield of 2‐formylarylsulphonates and tolerates variety of functional groups. The strategy opens a new avenue for the direct synthesis of ortho‐hydroxyl‐protected aryl aldehydes in organic synthesis.

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“…In 2011, Ghandi's group reported the stepwise synthesis of 3-substituted sulfocoumarins from salicylaldehydes and alkenesulfonyl chlorides (Scheme 1b). 9 These two methods are mainly restricted by the inconvenient routes to access the sulfonyl reagents. In 2012, in response to the irreproducibility of literature procedures, 10 Zalubovskis et al developed an efficient procedure to prepare 3, 4- featured the mesylation of salicylaldehydes, a DBU-catalyzed aldol-type condensation, and POCl 3 -mediated dehydration (Scheme 1c).…”

Section: Figure 1 Representative Bioactive Sulfocoumarins Reported Bymentioning

confidence: 99%

A Tandem Sulfonylation and Knoevenagel Condensation for the Preparation of Sulfocoumarin-3-carboxylates

Dong

Yang

et al. 2019

Synthesis

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Sulfocoumarins are key structural motifs in several bioactive molecules. Herein, we describe a simple, one-pot procedure for the synthesis of structurally diverse sulfonocoumarin-3-carboxylates by heating 2-hydroxyaryl aldehydes with an active sulfonyl chloride in the presence of pyridine. The process tolerates numerous functional groups including alkoxy, alkyl, halogen, nitro, and even nucleophilic phenolic hydroxy. Additionally, reactions of 2-hydroxyaryl ketones and 2-methylaminoaryl aldehydes give 4-substituted sulfocoumarins and 1-aza-2-sulfocoumarins, respectively. A gram-scale synthesis and further derivatizations are also reported. The ester group is easily removed via Happer’s decarboxylation.

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Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences

Cited by 20 publications

References 70 publications

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

2‐Formylarylsulfonate from Aryne: A Sequential Reaction Strategy for Direct Synthesis of ortho‐Hydroxyl‐Protected Aryl Aldehydes

A Tandem Sulfonylation and Knoevenagel Condensation for the Preparation of Sulfocoumarin-3-carboxylates

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