Synthesis of 2-trifluoromethyl chromenes <i>via</i> double carbonyl–ene reaction

Chen, Shouxiong; Wang, Hui; Lin, Qi; Weng, Zhiqiang

doi:10.1039/d1qo01766g

Cited by 4 publications

(1 citation statement)

References 31 publications

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“…The synthetic tricyclic chromene with the exocyclic benzylidene moiety also showed strong antileishmanial acitivity . As a result, the development of elegant synthetic methodologies for diverse chromane derivatives is a highly active area in organic synthesis. , Until now, many efforts have been devoted to the access of various polysubstituted chromanes. , However, there are still some shortcomings in the known synthetic methods for multifunctionalized chromene derivatives. , Development of efficient, green, and environment-friendly synthetic protocols for diverse chromene derivatives is very necessary …”

Section: Introductionmentioning

confidence: 99%

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

He,

Huang,

Huang

et al. 2024

J. Org. Chem.

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A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing o-hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-(o-hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro [cyclobuta[c]chromene-1,3′-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields. In addition, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 2-(o-hydroxyarylidene)-1,3-indanediones in tetrahydrofuran at 60 °C resulted in complex indeno[2′,1′:5,6]pyrano [3,4-c]chromene derivatives in high yields and with high diastereoselectivity.

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Section: Introductionmentioning

confidence: 99%

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

He,

Huang,

Huang

et al. 2024

J. Org. Chem.

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Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates

Barata‐Vallejo,

Yerien,

Zottola

et al. 2024

Eur J Org Chem

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The direct addition of perfluoroacyl (‐CORF) groups to organic frameworks has seen a resurgence in interest due to the benefits of these groups in late‐stage modification of pro‐drugs and biologically active compounds, helping to identify new active leads. The presence of ‐CORF groups positively impacts the structure‐activity relationships of these compounds. In that sense, both polar methods and radical catalytic protocols have been developed for the direct syntheses of trifluoromethyl and perfluoroalkyl ketones. In particular, methodologies to tame the unstable trifluoroacyl radical, which could be a key intermediate in the late‐stage syntheses of trifluoroacyl‐substituted compounds, has allowed much progress in this area. In the next sections, the direct incorporation of perfluoroacyl groups into (hetero)aromatic compounds, ‐CORF substitutions at Csp3‐H, alkyl halides, alkenes, amides, and N‐atoms will be discussed in detail, suggesting the future directions and perspectives in the field. These known reactions are summarized in Table 1.

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Copper Loading-Controlled Selective Synthesis of 2,5-Bis(trifluoromethyl) and Monotrifluoromethyl-Substituted Oxazoles

Wu,

Zhang,

et al. 2023

J. Org. Chem.

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A general domino annulation reaction of sulfonylmethyl isocyanide with trifluoroacetic anhydride in the presence of copper chloride as an additive is developed. The reaction affords 2,5-bis(trifluoromethyl)oxazoles in modest to good yields under mild conditions. A wide variety of sulfonylmethyl isocyanide and perfluorocarboxylic anhydride substrates are amenable to this transformation. Under a higher copper salt loading conditions, the reaction led to the formation of monotrifluoromethyl-substituted oxazole product.

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Synthesis of 2-trifluoromethyl chromenes via double carbonyl–ene reaction

Abstract: A new protocol for the synthesis of diversely substituted 2-trifluoromethyl chromenes from the cyclization reaction of o-isopropenylphenols with trifluoroacetic anhydride has been developed, which proceeds via sequential trifluoroacetylation and double...

Cited by 4 publications

References 31 publications

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates

Copper Loading-Controlled Selective Synthesis of 2,5-Bis(trifluoromethyl) and Monotrifluoromethyl-Substituted Oxazoles

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