Aromatic Electrophilic Substitution vs. Intramolecular Wittig Reaction: Vinyltriphenylphosphonium Salt Mediated Synthesis of 4-Carboxyalkyl-8-formyl Coumarins

Majumdar, K. C.; Ansary, Inul; Samanta, Srikanta; Roy, B.

doi:10.1055/s-0030-1259534

Cited by 14 publications

(8 citation statements)

References 13 publications

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“…Substituted 2-hydroxybenzaldehydes react with phenylacetic acids resulting in substituted 3-aryl coumarins [30]. With dialkyl acetylenedicarboxylate, 2-hydroxybenzaldehydes gives 4-carboxyalkyl-8-formyl coumarins [31]. 2-Hydroxybenzaldehydes (or 2-hydroxybenzaldehydes) cyclizes with aryl acetic acids to give 3-aryl coumarins (or 3-aryl-4-methyl-coumarins) [32] (Figure 12).…”

Section: Synthesis Of Coumarinsmentioning

confidence: 99%

The Oxygen-Containing Fused Heterocyclic Compounds

Venkatachalam¹,

N²

2020

Heterocycles - Synthesis and Biological Activities

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The oxygen-containing heterocycles are an important class of compounds in organic chemistry. These compounds are used as drugs (coumarin and oxazole), solvent (tetrahydrofuran), flavors, and fragrances (lactones). The fusion of aromatic ring to the oxygen-heterocycle will change the electron density; thereby, the physical/chemical/biological properties will alter. Also, the preparation of these fused molecules will require a different strategy/method/reaction condition. The topics covered in this chapter are the general synthetic methods and uses of fused heterocyclic compounds containing oxygen as a heteroatom. The derivatization of the primary scaffold is excluded from this chapter. Some of the fused compounds are coumarin (benzopyrans) and piclozotan (benzoxazepines).

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Section: Synthesis Of Coumarinsmentioning

confidence: 99%

The Oxygen-Containing Fused Heterocyclic Compounds

Venkatachalam¹,

N²

2020

Heterocycles - Synthesis and Biological Activities

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“…However, reactions of di-and trihydric phenols with dimethyl acetylenedicarboxylate (DMAD) in the presence of triphenylphosphine in toluene under reflux afford polyfunctionalized coumarin analogues along with unwanted by-products in appreciable amount (Figure 26) [113]. (Figure 27) [114].…”

Section: Vinyl Phosphonium Salt-mediated Electrophilic Substitution Rmentioning

confidence: 99%

One-Pot Synthesis of Coumarin Derivatives

Ansary¹,

Taher²

2020

Phytochemicals in Human Health

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Coumarin derivatives have a myriad of applications in medical science, biomedical research, and many industrial branches. For this reason, many efforts are being dedicated to the development of novel and more practical methods for synthesizing these compounds. This chapter describes several methods of one-pot synthesis of coumarin derivatives, including von Pechmann condensation, Knoevenagel condensation, Baylis-Hillman reaction, Michael addition, Kostanecki reaction, vinyl phosphonium salt-mediated electrophilic reaction, and Heck-lactonization reaction. The methods are compared with each other, and the advantages and disadvantages of each of them are addressed.

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“…The synthesis of 4-carboxyalkyl-8-formyl coumarins have also been developed with the reaction of 2-hydroxybenzaldehydes and triphenylphosphine and dialkyl acetylene dicarboxylate 30 .…”

Section: Fig 7: Synthesis Scheme Of Coumarins Using Hydroxyl Benzaldmentioning

confidence: 99%

Untitled

2019

IJPSR

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Indole and coumarin are the most versatile and cogent heterocyclic scaffolds which are not only decisively used in the synthesis of various organic compounds but also play a consequence role in natural product synthesis, modulation of biofilm formation, virulence and stress responses. In last few decades, an individual has witnessed considerable activity towards the synthesis of indole derivatives due to the possibilities for the design of polycyclic structures by the incorporation of multiple fused heterocyclic scaffolds in an attempt to achieve promising new heterocycles with chemical and biomedical relevance. Whereas, coumarin is a 2-oxo-2H-1-benzopyran and, also, have a wide range of application in the pharmaceutical field. In this review, we provide an overview of the synthesis of coumarin and indoles and their pharmacological evolution. The coumarin was synthesized using phenols, salicylaldehyde, benzaldehyde, phenylacetate, styrenes, and cinnamic acid with different catalyst and photocatalyst to give the best yield. Similarly, Indoles were synthesized iodobenzoic acid, alkynes, amines, alcohols, Nitrobenzaldehyde with the different catalyst under conventional and irradiation method. The effect of various catalytic medium, solvents and operational condition are discussed for obtaining the best yield. A comparative account of various reaction pathways like one-pot synthesis (Multicomponent reaction) and the multistep reaction of coumarin and indoles are discussed. INTRODUCTION: Coumarins belong to a large family of heterocyclic compounds with a benzo-apyrone moiety, of natural and synthetic origin. Coumarin is the most representative molecule are widely distributed in plants like tonka bean (Dipteryx odorata Wild). It has been extensively used in biochemical and pharmaceutical fields 1 .

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Aromatic Electrophilic Substitution vs. Intramolecular Wittig Reaction: Vinyltriphenylphosphonium Salt Mediated Synthesis of 4-Carboxyalkyl-8-formyl Coumarins

Cited by 14 publications

References 13 publications

The Oxygen-Containing Fused Heterocyclic Compounds

The Oxygen-Containing Fused Heterocyclic Compounds

One-Pot Synthesis of Coumarin Derivatives

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