Three-component coupling using arynes and DMF: straightforward access to coumarins via ortho-quinone methides

Often used as a common solvent for chemical reations and utilized widely in industry as a reagent, N,N-dimethylformamide (DMF) has played an important role in organic synthesis for a long time. Numerous highly useful articles and reviews discussing its utilizations have been published. With a focus on the performance of DMF as a multipurpose precursor for various units in numerous reactions, this Minireview summarizes recent developments in the employment of DMF in the fields of formylation, aminocarbonylation, amination, amidation, and cyanation, as well as its reaction with arynes.

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“…[48] Arylacetonitriles were found to be suitable as Scheme 27. Proposed mechanism for the direct transformation of DMF into a CN group.…”

Section: Reactions With Arynesmentioning

confidence: 99%

N,N‐Dimethylformamide: A Multipurpose Building Block

2012

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“…[9] Bifunctional α-amino carbonitriles are not only key intermediates in the preparation of α-amino acids, but they also play important roles in constructing various heterocycles because of their dual functionality. [9] Bifunctional α-amino carbonitriles are not only key intermediates in the preparation of α-amino acids, but they also play important roles in constructing various heterocycles because of their dual functionality.…”

Section: Introductionmentioning

confidence: 99%

Three‐Component Synthesis of α‐Amino‐α‐aryl Carbonitriles from Arynes, Aroyl Cyanides, and N,N‐Dimethylformamide

et al. 2014

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A general and efficient synthesis of α‐amino‐α‐aryl carbonitriles through the three‐component reaction of arynes, aroyl cyanides, and DMF in a single step is described. DMF was not only used as the solvent, but it also participated in the reaction as a component. Used as the cyanide sources, the aroyl cyanides solved the toxicity and solubility problems associated with the use of HCN or metal cyanides in the Strecker synthesis. This procedure furnished α‐amino‐α‐aryl carbonitriles in moderate to good yields with broad substrate scope. Moreover, this reaction could be performed under mild conditions with high atom economy.

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“…hydrochloric acid and ethanol. Yoshida et al [77], have also been reported the synthesis of 173a through the reaction of 1 with 2-(trimethylsilyl)phenyl-trifluoro-methane-sulfonate (174) in DMF containing potassium fluoride (Scheme 38).…”

Section: Synthesis Of Coumarin Derivativesmentioning

confidence: 96%

Recent Progress in the Chemistry of 2-Tosylacetonitrile

Fadda

Bayoumy

Elattar

2015

Synthetic Communications

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This review reported a broad overview on the chemistry of 2-tosylacetonitrile which considered as a very reactive synthetic compound. The synthetic methods of synthesis were reported. The reactions of the title compound led to the preparation of a variety of heterocyclic ring systems i.e. five and six membered ring systems containing one or two or three heteroatoms. The reaction mechanisms were discussed. The bibliography includes mainly 124 references.

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Three-component coupling using arynes and DMF: straightforward access to coumarins via ortho-quinone methides

Abstract: ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner.

Cited by 122 publications

References 25 publications

N,N‐Dimethylformamide: A Multipurpose Building Block

N,N‐Dimethylformamide: A Multipurpose Building Block

Three‐Component Synthesis of α‐Amino‐α‐aryl Carbonitriles from Arynes, Aroyl Cyanides, and N,N‐Dimethylformamide

Recent Progress in the Chemistry of 2-Tosylacetonitrile

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