Biorenewable and mercaptoacetylating building blocks in the Biginelli reaction: synthesis of thiosugar-annulated dihydropyrimidines

Yadav, Lal Dhar S.; Awasthi, Chhama; Vijai, K.; Rai, Ankita

doi:10.1016/j.tetlet.2007.05.057

Cited by 45 publications

(25 citation statements)

References 31 publications

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“…Therefore, novel strategies are being devised to generate future generation cephalosporins [38]. In addition to broad spectrum activities, 1,3-thiazine and its derivatives contains wonderful properties like antitumor, insecticide, and fungicidal [19,20,40,41]. Further, these can be used as anti-radiation agents in radiation-sickness [19,20,40,41].…”

Section: Biological Activities Of Thiazine and Benzothiazine Derivmentioning

confidence: 99%

Bioactive Thiazine and Benzothiazine Derivatives: Green Synthesis Methods and Their Medicinal Importance

Badshah

Akhtar

2016

Molecules

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Abstract:Thiazines are a group of heterocyclic organic compounds that are still largely unexplored for their pharmacological activities. There are different available methods for the synthesis of thiazine derivatives in the literature. In this review, we discuss available methods of thiazine preparation through green synthesis methods. Beside their synthesis, many thiazine derivatives are biologically active and play an important role in the treatment of various diseases and show promising results of varying degrees, where they act as antibacterial, antifungal, antitumor, antimalarial, antineoplastic, antiviral, anti-inflammatory, analgesic and anticancer agents and thus they represent an interesting class of heterocyclic medicinal compounds worthy of further exploration.

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Section: Biological Activities Of Thiazine and Benzothiazine Derivmentioning

confidence: 99%

Bioactive Thiazine and Benzothiazine Derivatives: Green Synthesis Methods and Their Medicinal Importance

Badshah

Akhtar

2016

Molecules

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“…187 As a recent and nice example, Yadav et al have developed a novel efficient version of diastereoselective Biginelli reaction which involved a mercaptoacetylating active methylene building block, unprotected aldoses as biorenewable aldehyde components, and ureas or thioureas. 188 As shown in Scheme 1.112, the process allowed a range of thio-sugar-annulated multifunctionalised dihydropyridine scaffolds of pharmaceutical potential, arising from the use of D-xylose and D-glucose as aldoses. This reaction was performed without solvent under microwave irradiation at 90 1C in the presence of Montmorillonite K-10 nanoclay and provided these important chiral products in high general yields combined with high diastereoselectivities of up to 96% de.…”

Section: Multicomponent Reactions Based On the Biginelli Reactionmentioning

confidence: 99%

Asymmetric Domino Reactions Based on the Use of Chiral Substrates

2013

Asymmetric Domino Reactions

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This chapter updates the recent developments in asymmetric one-, two-, and multicomponent domino reactions which involve chiral substrates. It is divided into two sections, dealing successively with one- and two-component domino reactions, and with multicomponent domino reactions. The first section is subdivided into eight sections, describing domino reactions with an anionic primary step, domino reactions based on cationic sequences, domino reactions initiated by a pericyclic primary step, domino reactions based on carbene sequences, palladium-catalysed domino reactions, ruthenium-catalysed domino reactions, gold-catalysed domino reactions, and finally miscellaneous domino reactions. The second section of the chapter is subdivided into 10 sections, dealing with multicomponent reactions initiated by the Michael addition, multicomponent reactions based on the Hantzsch reaction, multicomponent reactions based on the Ugi reaction, multicomponent reactions based on the Strecker reaction, multicomponent reactions based on the Mannich reaction, multicomponent reactions initiated by an allylation reaction, multicomponent reactions based on the Passerini reaction, multicomponent reactions based on the Biginelli reaction, multicomponent reactions based on the Petasis reaction, and finally miscellaneous multicomponent reactions. The power and utility of these reactions are well illustrated by their application in the synthesis of a wide range of structurally diverse and complex chiral molecules.

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“…El Ashry et al [74] also achieved the high-yielding synthesis of derivatives 123a,b, which were used to obtain the respective triazolylglycosides (127a-f) by reaction with glycosyl halides (124-126) in dry acetone in the presence of K 2 CO 3 as base, under both CH and MWI conditions (scheme 21.35). Following their interest in devising new one-pot, solvent-free cyclization procedures under MWI, especially involving stereocontrolled protocols with unprotected aldose as a biorenewable aldehyde component, Yadav et al [75] reported a novel nanoclay-catalyzed version of the Biginelli reaction, allowing the reaction of an unprotected aldose, a 3-oxathiolan-5-one, and amidines/ guanidine. Thio sugar-annulated multifunctionalized dihydropyrimidines were obtained diastereoselectively via intramolecular domino cyclocondensations of an isolable intermediate.…”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%