Synthesis of carbazoles by a balanced four component condensation

Cochard, Fabien; Laronze, Marie; Sigaut, Philippe; Sápi, János; Laronze, Jean‐Yves

doi:10.1016/j.tetlet.2003.12.099

Cited by 30 publications

(9 citation statements)

References 22 publications

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“…As examples, condensation of indole,167 or more recently indolin‐2‐one,168 with Meldrum’s acid and various aldehydes resulted in the one‐pot syntheses of ethyl indolylpropionates and of spiro[pyrrolidine‐3,3′‐indolinones], respectively, in a so‐called Yonemitsu condensation. Extending this three‐component reaction to 2‐substituted indoles, Sati and co‐workers recently reported an easy access to functionalised tetrahydrocarbazoles 169. Finally, a variant of this reaction consisting of the diastereoselective trimolecular condensation of indole, Meldrum’s acid and Garner’s aldehyde (Scheme ) was reported as a key step in the synthesis of chiral 2′,3′‐pyranone(pyrrolidinone)‐fused tryptamines 170…”

Section: Mcrs Based On the Knoevenagel Reactionmentioning

confidence: 99%

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

2004

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Although isocyanide‐based multicomponent reactions (MCRs), introduced in 1921 by Passerini, largely predominate nowadays in the construction of widely diverse heterocycles, one of the first substrate classes involved in a MCR was that of 1,3‐dicarbonyl derivatives, with Hantzsch’s dihydropyridine synthesis appearing as early as 1882. The aim of this microreview is to present an overview of the great synthetic potential of MCRs involving the specific reactivity of easily accessible 1,3‐dicarbonyl derivatives and to stress their more recent utilisation for the development of new and useful methodologies valuable for the selective construction of highly functionalised small organic molecules of high synthetic and biological value. After a short general introduction, we present chronologically the different methodologies developed on the bases of the reactivity of 1,3‐dicarbonyl systems towards many other substrates involved in a variety of synthetic pathways, including Knoevenagel condensations, Michael and Mannich reactions, cyclodehydrations, electrocyclisations, cycloadditions and metal‐promoted transformations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Mcrs Based On the Knoevenagel Reactionmentioning

confidence: 99%

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

2004

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“…For the synthesis of heterocyclic compounds, see: Scott & Raston (2000); Alvim et al (2005); Fillion & Dumas (2008). For combinatorial synthesis, see: Shaabani et al (2004); Wang et al (2007); Cochard et al (2004). For puckering parameters, see: Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

“…The 5-arylidenes Meldrum's acid derivatives, like title compound, are versatile intermediates in organic synthesis, for example, this type of compounds were used in hetero-Diels-Alder reaction (Palasz et al 2007;Fillion et al 2006 andMizukami et al 1993), as well as in the synthesis of heterocycle compound, like coumarins (Scott et al 2000 andAlvim et al 2005); γ-Butyrolactones and pyrrole derivatives (Fillion et al 2008). Also, the 5-arylidene derivatives of Meldrum's acid possess an α, β-unsaturated carbonyl system, which is considered as a key building block in combinatorial reaction for three components synthesis (Shaabani et al 2004 andWang et al 2007), alike four components reaction (Cochard et al 2004). The title compound was obtained by a green Knoevenagel condensation of Meldrum acid with 2-nitrobenzaldehyde employing ultrasonic radiation and water as solvent.…”

Section: S1 Commentmentioning

confidence: 99%

2,2-Dimethyl-5-(2-nitrobenzylidene)-1,3-dioxane-4,6-dione

et al. 2012

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Key indicators: single-crystal X-ray study; T = 130 K; mean (C-C) = 0.002 Å; R factor = 0.035; wR factor = 0.088; data-to-parameter ratio = 12.4.The asymmetric unit of the title compound, C 13 H 11 NO 6 , contains two molecules in both of which the six-membered 1,3-dioxane-4,6-dione ring shows a screw-boat conformation. The dihedral angles between the best planes through the sixmembered rings are 47.8 (2) and 49.8 (2) . In the crystal, C-HÁ Á ÁO interactions link the molecules, building a supramolecular sheet parallel to the c axis. Related literature ExperimentalCrystal data

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“…They also extended the reaction to 2-substituted indoles (73) and, by altering the reaction conditions, a variety of new scaffolds (74 -77) were obtained (Scheme 15) [25].…”

Section: Alkylidene Meldrums Acid Precursorsmentioning

confidence: 99%

Meldrum's Acid in Multicomponent Reactions: Applications to Combinatorial and Diversity‐Oriented Synthesis

Gerencsér¹,

Dormán²,

Darvas³

2006

QSAR Comb. Sci.

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In a multicomponent reaction (MCR), one can create multiple new bonds in a single reaction from readily available starting materials; thus, MCRs are resource-and timeeffective and therefore economically favorable processes in diversity generation. In contrast, there are MCRs where a multifunctional building block is introduced instead of an additional diversity-holding component, and these can be derivatized using very diverse reactions post-synthetically leading to novel chemotypes. The synthetic applications of Meldrums acid are focusing primarily on reactions where it is applied as an alternative for acyclic malonic esters. However, its highly acidic character broadened its applications and made it a very useful reagent for MCRs or more precisely in tandem or domino reactions. There are numerous examples reported for the use of the alkylidene conjugates of Meldrums acid as dienophiles in hetero-Diels -Alder reactions, as well as Michael acceptors. In most cases spontaneous or concomitant post-synthetic derivatization increased its synthetic utility. This minireview gives a non-exhaustive insight into MCRs involving Meldrums acid, describing various applications in combinatorial and diversityoriented synthesis.

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Synthesis of carbazoles by a balanced four component condensation

Cited by 30 publications

References 22 publications

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

2,2-Dimethyl-5-(2-nitrobenzylidene)-1,3-dioxane-4,6-dione

Meldrum's Acid in Multicomponent Reactions: Applications to Combinatorial and Diversity‐Oriented Synthesis

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