Bismuth triflate catalyzed condensation of δ-hydroxy-α,β-unsaturated aldehydes with aryl amines

Yadav, J. S.; Reddy, B. V. Subba; Parimala, G.; Raju, Atla

doi:10.1016/j.tetlet.2003.12.043

Cited by 25 publications

(10 citation statements)

References 14 publications

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“…In the presence of Bi(OTf) 3 , in CH 3 CN at 80 o C, -hydroxy-, -unsaturated aldehydes and aryl amines underwent the tandem Michael and intramolecular Friedel-Crafts type cyclization to produce a new class of chiral tetrahydroquinolines in good yields with high stereoselectivity. This method is quite simple and straightforward and constructs unusual benzo-fused heterobicycles in a single-step operation (Scheme 32) [43]. Among the examined various metal triflates such as In(OTf) 3 , Ce(OTf) 3 , Sc(OTf) 3 , Yb(OTf) 3 and Bi(OTf) 3 , Bi(OTf) 3 was found to be the most effective catalyst for this transformation.…”

Section: Bismuth-catalyzed Carbon-carbon Bond Formationmentioning

confidence: 98%

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Hua

2008

COS

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Section: Bismuth-catalyzed Carbon-carbon Bond Formationmentioning

confidence: 98%

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Hua

2008

COS

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“…Bi(OTf) 3 was found to be an efficient catalyst for the tandem Michael followed by intramolecular Friedel‐Crafts type cyclization of δ‐hydroxyl group containing α,β‐unsaturated aldehydes ( 91 ) with arylamines ( 13 ) to afford a new class of stereoselective tetrahydroquinolines ( 92 ) in good yields (Table ) …”

Section: Bi(otf)3 Catalyzed Synthesis Of N and O‐heterocyclesmentioning

confidence: 99%

Bismuth(III) triflate: An Efficient Catalyst for the Synthesis of Diverse Biologically Relevant Heterocycles

Banerjee¹

2017

ChemistrySelect

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Last decade has seen a tremendous applications of bismuth(III) trifluoromethanesulfonate [Bi(OTf)3] as an efficient, cheap, environmentally benign, Lewis acidic catalyst for the various organic transformations. On the other hand heterocycles are very common in naturally occurring compounds and are the privileged structural subunit of many marketed drug molecules. The present review summarizes the applications of bismuth(III) triflate as a catalyst for the synthesis of diverse biologically relevant heterocycles reported so far.

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“…The Yadav group has reported that a,b-unsaturated aldehydes bearing d-hydroxyl group undergo a tandem Michael and intramolecular Friedel-Crafts type cyclization with arylamines in the presence of Bi(OTf) 3 to afford tetrahydroquinolines in good yields (Scheme 54). 97 Bi(OTf) 3 was found to be more effective than In(OTf) 3 for these transformations.…”

Section: Synthesis Of Tetrahydroquinolinesmentioning

confidence: 90%

Applications of bismuth(iii) compounds in organic synthesis

2011

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8388 5.3. Formation of acetals catalyzed by bismuth(III) triflate 8388 5.4. Formation of 1,l-diacetates (acylals) 8389 5.5. Cleavage of epoxides catalyzed by bismuth(III) chloride 8389 5.6. Glycosylation promoted by bismuth(III) chloride 8389 5.7. Selective hydrolysis of aryl esters using bismuth(III) mandelate 5.8. Carbon-sulfur bond formation 5.8.1. Synthesis of thioacetals 8389 5.8.2. Conversion of epoxides to thiiranes 8390 5.9. Sulfonylation of aromatics 8390 5.10. Synthesis of sulfides and selenides promoted by Sm-BiCI3 8391 5.11. Synthesis of allyl sulfides 8391 5. 12. Formation of carbon-halogen bonds 8391 5.12.1. Synthesis of �-haloketones and esters 8391 5.12.2. Chlorination of alcohols catalyzed by bismuth(III) salts 8391 5.12.3. Synthesis of peracetylated glycosyl halides 8392 6. Reductions with bismuth compounds 8392 6.1. Selective reduction of nitro compounds to azoxy compounds 8392 6.2. Reduction of nitro compounds to amines 8392 6.3. Chemoselective reduction of a,�-unsaturated ethyl esters using BiCI3-NaBH 4 8392 6.4. Reduction of aromatic a-haloketones 8393 6.5. Miscellaneous reductions 8393 7. Rearrangements promoted by bismuth(III) salts 8393 7.1. Rearrangement of epoxides 8393 7.2. Allylic rearrangement of glycols (the Ferrier rearrangement) 8394 8. Conclusions

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Bismuth triflate catalyzed condensation of δ-hydroxy-α,β-unsaturated aldehydes with aryl amines

Cited by 25 publications

References 14 publications

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Bismuth(III) triflate: An Efficient Catalyst for the Synthesis of Diverse Biologically Relevant Heterocycles

Applications of bismuth(iii) compounds in organic synthesis

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