A facile access to substituted indoles utilizing palladium catalyzed annulation under microwave enhanced conditions

Karuvalam, Ranjith P.; Haridas, Karickal R.; Sajith, Ayyiliath M.; Muralidharan, A.

doi:10.1016/j.tetlet.2013.07.073

Cited by 19 publications

(4 citation statements)

References 18 publications

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“…We then decided to treat the intermediate 3b with different primary and secondary amines 4a-h in view of synthesizing more decorated oxazole based target molecules. Microwave irradiation reactions are always considered to be superior to conventional heating methodologies owing to its rapid product formation with lesser side-products [14][15][16][17][18][19][20]. Accordingly, we decided to utilize microwave irradiation for the synthesis of our target molecules.…”

Section: Procedures (Filtration) Was Facile and Efficient In Terms Of Yield And Time Consumptionmentioning

confidence: 99%

A modified approach for the synthesis of biologically relevant 5-substituted-2-N-aryl-1,3-oxazole derivatives in mild conditions

Udhayasurian

Sivakumar²,

Sajith

et al. 2020

Journal of Taibah University for Science

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We herein report a modified approach for the synthesis of some pharmacologically relevant oxazole derivatives linked with amides under mild conditions. The utilization of polymer-supported triphenylphosphine (poly-TPP) as a phosphine ligand for generating the key iminophosphorane intermediate was found to be vital for achieving the synthesis of oxazole in room temperature. This alternative approach relying on the cyclization reaction of readily available phenacyl azide and phenyl isothiocyanate rendered the oxazole derivative 3a in excellent yield. This methodology has been applied for the synthesis of a more decorated oxazole derivative 3b having ester functionality and was further converted to different amides under microwave irradiation in good to excellent yields in the later stage.

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Section: Procedures (Filtration) Was Facile and Efficient In Terms Of Yield And Time Consumptionmentioning

confidence: 99%

A modified approach for the synthesis of biologically relevant 5-substituted-2-N-aryl-1,3-oxazole derivatives in mild conditions

Udhayasurian

Sivakumar²,

Sajith

et al. 2020

Journal of Taibah University for Science

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“…Among heterocyclic systems, the benzimidazole core is found in many biologically relevant molecules which requires the functionalization of this framework using palladiummediated cross-coupling reactions. [9][10][11][12][13][14][15][16] As a part of our research efforts towards developing protocols that incorporate structural diversity into a heteroaromatic system, [17][18][19][20][21][22][23][24][25][26] we envisioned a Suzuki-Miyaura crosscoupling methodology to access 2-aryl/heteroaryl-substituted benzimidazoles. In recent years, the use of microwave energy in organic synthesis has gained much popularity in both industrial and academic research.…”

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura coupling under microwave enhanced conditions: synthesis of 2-(hetero)aryl benzimidazoles

Karuvalam¹,

Haridas²,

Sajith³

et al. 2020

Arkivoc

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An expedient, palladium-mediated cross-coupling approach to functionalize the benzimidazole-based core under microwave-assisted conditions has been developed and is described. This protocol, which incorporates appendage diversity on this potential scaffold, is found to be compatible with a wide range of electronicallyand sterically-divergent (hetero)aryl boronic acids. The use of the PdCl 2 /(SPhos) catalytic system allows the formation of a stable and highly active LPd(0) species which was found to be critical for the successful synthesis of these novel, pharmacologically-relevant molecules.

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“…Diversely substituted heterocycles have vast application in the field of medicinal chemistry, as a number of heterocyclic derived analogues exhibit important biological properties. Diversity oriented synthesis (DOS) approach is a requirement in modern drug discovery programs as it enables the elaboration of a functional group into a diverse range of molecular structures.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Fully Decorated Imidazo[4,5‐b] and Imidazo[4,5‐c] Pyridines in Aqueous DMF via C‐H Activation under Microwave Irradiation

et al. 2016

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Catalytic C−H bond activation of heteroarenes has gained tremendous potential in recent years due to their environmentally and economically benign nature. In this paper we report the regioisomeric synthesis of fully decorated imidazo pyridines employing a C−H activation protocol with a wide range of aryl/hetero aryl/alkyl boronic acids in aqueous DMF. The use of inexpensive copper catalyst and Bathophenanthroline as ligand were found to be instrumental in driving these reactions to completion. This optimised protocol was further extended to alkyl/aryl/heteroaryl potassium organo trifluoroborates. A wide range of diversely substituted imidazo pyridine analogues which are known for their potential therapeutic applications have been synthesized using this highly efficient and atom economical protocol.

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A facile access to substituted indoles utilizing palladium catalyzed annulation under microwave enhanced conditions

Cited by 19 publications

References 18 publications

A modified approach for the synthesis of biologically relevant 5-substituted-2-N-aryl-1,3-oxazole derivatives in mild conditions

A modified approach for the synthesis of biologically relevant 5-substituted-2-N-aryl-1,3-oxazole derivatives in mild conditions

Suzuki-Miyaura coupling under microwave enhanced conditions: synthesis of 2-(hetero)aryl benzimidazoles

Facile Synthesis of Fully Decorated Imidazo[4,5‐b] and Imidazo[4,5‐c] Pyridines in Aqueous DMF via C‐H Activation under Microwave Irradiation

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