An efficient one-pot synthesis of coumarins mediated by propylphosphonic anhydride (T3P) via the Perkin condensation

Augustine, John Kallikat; Bombrun, Agnès; Ramappa, Balakrishna Kolathur; Chandrakantha, B.

doi:10.1016/j.tetlet.2012.06.037

Cited by 70 publications

(30 citation statements)

References 29 publications

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“…5,6 Similarly benzoiminocoumarins (8)(9)(10)14, and 15) were synthesized using malononitrile as the active methylene component. 5,6 Similarly benzoiminocoumarins (8)(9)(10)14, and 15) were synthesized using malononitrile as the active methylene component.…”

Section: Scheme 3 Synthesis Of Benzo[g]coumarins Through the Knoevenamentioning

confidence: 99%

π-Expanded coumarins: synthesis, optical properties and applications

et al. 2015

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Coumarins fused with other aromatic units have recently emerged as a hot topic of research. Their synthesis is partly based on classical methodologies such as Pechmann reaction or Knoevenagel condensation, but it also sparked the discovery of completely new pathways. In very recent years so-called vertically-expanded coumarins were synthesized, effectively expanding the portfolio of existing architectures. A subtle relationship exists between the structure of fused coumarins and their optical properties. Although absorption of UV-radiation and light is unifying theme among these π-expanded coumarins, the fluorescence properties strongly depend on the structure. The mode of fusion, the type of additional ring and the presence of electron-donating and electron-withdrawing substituents all influence the photophysical parameters. Recent advances made it possible to modulate their absorption from 300 nm to 550 nm, resulting in new coumarins emitting orange light. This review serves as a guide through both synthesis strategies and structure-property relationship nuances. Strong intramolecular charge-transfer character made it possible to reach suitable values of two-photon absorption crosssection. Photophysical advantages of π-expanded coumarins have been already utilized in fluorescence probes and two-photon excited fluorescence microscopy.

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Section: Scheme 3 Synthesis Of Benzo[g]coumarins Through the Knoevenamentioning

confidence: 99%

π-Expanded coumarins: synthesis, optical properties and applications

et al. 2015

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“…The salicylaldehyde derivatives were frequently applied in the cyclization with arylacetic acids (Eq. 23‐2) –. Their mechanism usually involved a sequence of nucleophilic addition and intramolecular cyclization.…”

Section: Nucleophilic Methylenesmentioning

confidence: 99%

“…Two pathways attributed to the same products, which were determined by different conditions. DCC, PPh 3 /I 2 , CDI, propylphosphonic anhydride (T 3 P), and Mukaiyama's reagent acted as promoters in the formation of ester intermediates 22.3 (pathway B). If only a base was used, aldol reactions occurred to give 22.2 in the transformation (pathway A) (Scheme ).…”

Section: Nucleophilic Methylenesmentioning

confidence: 99%

Arylacetic Acids in Organic Synthesis

et al. 2019

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Arylacetic acids are widely used in organic reactions and their recent advances are summarized in six categories according to their triggered pathways: (1) the acid as directing group in ortho-or meta-CÀ H activation; (2) decarboxylation; (3) deprotonation; (4) nucleophilic methylenes; (5) nucleophilic acids; (6) electrophilic acids. Reactions with alkenes, alkynes, aldehydes, amines, water, Grignard reagents, silanes and so forth are discussed. We hope this Minireview will promote future research in this area. Recently, the Zeng group [3g] reported a weakly coordinationassisted alkynylation of arylacetic acids with iridium catalysis under air atmosphere (Eq. 2-2). It was supported the sixmembered ring cycloiridiated 2.5 acted as the key intermediate. The alkynylation of indole, thiophene, pyrrole, and benzo[b] thiophene afforded better yields than phenylacetic acids. The acid moiety could also participated in the intramolecular ortho-CÀ H activation, which was developed by the Shi group to obtain lactonization 2.6 (Eq. 2-3) (Scheme 2). Meta-CÀ H ArylationThe study of Yu group [3e] in 2017 revealed a successful control of meta selectivity 3.1 of arylation from aryl iodides (Eq. 3-1). The use of mono-protected 3-amino-2-hydroxypyridine (as ligand) and 2-carbomethoxynorbornene (NBE-CO 2 Me) were crucial. In the absence of NBE-CO 2 Me, only ortho-arylated product was obtained. This method was still efficient in a gramsale (Scheme 3). Decarboxylation Decarboxylative CouplingAs shown in Scheme 4, the decarboxylation could generate benzyl radicals 4.1. Then, direct couplings of 4.1 with diverse [ + ] These authors contributed equally. Scheme 1. Six categories based on triggered mechanism. 2 3 4 5 6 7 8 . Passerini Three-Component ReactionThe Passerini reaction was the oldest multicomponent reaction (MCR) [37d] in which isocyanides, carboxylic acids and aldehydes were used. It was powerful for the rapid construction of complex molecules. The tactic to expand the scope of Passerini reaction was to use surrogates of the carbonyl partners. As described in Scheme 51, syn-chlorooximes, [37b] diazoketones, [37c] alcohols, [37d,e] azirines [37f] and isatins [37g] could be employed instead of aryl or alkyl aldehydes [37a] (Scheme 51). Besides, in 2018, Zhang and co-workers [37] have firstly reported asymmetric phosphoric acid-catalyzed four-component Ugi reaction, which Scheme 45. BTM-catalyzed cycloaddition. Scheme 46. HBTM-catalyzed cycloaddition. Scheme 47. TFA-catalyzed reaction. Scheme 48. Friedel-Crafts triggered tandem reactions. Scheme 49. C-acylation of 1,3-diones. Scheme 50. C-acylation of 1,3-indandiones.

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“…In view of the pharmaceutical importance of heterocyclic compounds containing coumarin moiety, various approaches toward the synthesis of this class of compounds have been explored [13][14][15][16][17]. Although these methods are quite satisfactory, most of these methods suffer from extended reaction times, low yields, use of costly reagents, vigorous reaction conditions and also requirement of tedious work-up procedures.…”

Section: Introductionmentioning

confidence: 99%

Succinimide-N-sulfonic acid as an efficient recyclable catalyst for the synthesis of some fused indolo pyrano pyrimidinone derivatives

Mansoor¹,

Logaiya²,

Sudhan³

et al. 2015

Bull. Chem. Soc. Eth.

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ABSTRACT.A new, simple, thermally efficient and solvent-free condensation of 2-amino-4,5-dihydro-4-phenylpyrano[3,2-b]indole-3-carbonitrile derivatives with coumarin-3-carboxylic acid employing succinimide-Nsulfonic acid (SuSA) as catalyst for the synthesis of a series of 5,6-dihydro-2-(2-oxo-2H-chromen-3-yl)-5-phenylindolo[2',3':5,6]pyrano[2,3-d]pyrimidin-4(3H)-one derivatives is described. This method has the advantages of high yield, simple methodology, and short reaction time, as well as being green in terms of avoiding the use of toxic catalysts and solvents. Furthermore, the catalyst could be recycled and reused four times without significant loss of activity. Thiourea dioxide (TUD) catalyzed efficient three-component coupling reactions of aromatic aldehydes, 3-hydroxyindole and malononitrile in water at 70 ºC was described as the preparation of 2-amino-4,5-dihydro-4-phenylpyrano[3,2-b]indole-3-carbonitrile derivatives.

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An efficient one-pot synthesis of coumarins mediated by propylphosphonic anhydride (T3P) via the Perkin condensation

Cited by 70 publications

References 29 publications

π-Expanded coumarins: synthesis, optical properties and applications

π-Expanded coumarins: synthesis, optical properties and applications

Arylacetic Acids in Organic Synthesis

Succinimide-N-sulfonic acid as an efficient recyclable catalyst for the synthesis of some fused indolo pyrano pyrimidinone derivatives

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