Aromatization of 3,4-dihydro-β-carboline-3-qarboxylic acid and its derivatives through a carbanion intermediate : mechanistic study and use in chemical synthesis

Previero, A.; Barry, L.-G.; Torreilles, Jean; Fleury, B.; Letellier, S.; Maupas, B.

doi:10.1016/0040-4020(84)85124-8

Cited by 13 publications

(3 citation statements)

References 8 publications

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“…[4] A mechanism for the aromatization of 3,4-dihydro-β-carbolines under mildly basic conditions has been described. [20] Scheme 4…”

Section: Methodsmentioning

confidence: 99%

“…These syntheses both involved methyl 1-formyl-β-carboline-3-carboxylate (20), a useful precursor which was prepared in 54% yield, by a four-step procedure, from readily available L BischlerϪNapieralski reaction provides a valuable alternative pathway for the preparation of β-carbolines, but in this case, N b -acyltryptophan derivatives usually undergo intramolecular cyclization to form 3,4-dihydro-β-carbolines. However, there are examples in which N b -acyltryptophan esters have been converted into fully aromatic β-carbolines directly.…”

Section: Introductionmentioning

confidence: 99%

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Reactivity of β‐Carbolines and Cyclopenta[b]indolones Prepared from the Intramolecular Cyclization of 5(4H)‐Oxazolones Derived from L‐Tryptophan

Condie¹,

Bergman²

2004

Eur J Org Chem

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Keywords: 5(4H)-Oxazolone / β-Carboline / Cyclopenta [b]indolone / Cyclization / BischlerϪNapieralski reaction / Canthine / Synthesis design 4-(1H-Indol-3-ylmethyl)-2-trichloromethyl-1,3-oxazol-5(4H)-one (4) was shown to undergo an intramolecular reaction in the presence of TFA, to afford a β-carboline 5 and a cyclopenta[b]indolone 6 by nucleophilic addition at C-2 and C-5, respectively. The distribution of these two products was found to be dependent on the reaction temperature, with lower temperatures favouring the formation of the β-carboline 5. Subsequent reactions performed on the β-carboline 5 led to the formation of canthine and canthin-6-one derivatives.

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“…[4] A mechanism for the aromatization of 3,4-dihydro-β-carbolines under mildly basic conditions has been described. [20] Scheme 4…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Reactivity of β‐Carbolines and Cyclopenta[b]indolones Prepared from the Intramolecular Cyclization of 5(4H)‐Oxazolones Derived from L‐Tryptophan

Condie¹,

Bergman²

2004

Eur J Org Chem

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“…It is worth mentioning that the 0-carboline moiety is widely distributed in natural biologically active compounds and constitutes the key structure of several synthetic products of pharmacological interest (15,16).…”

mentioning

confidence: 99%

Chymotrypsin catalysed synthesis of fluorescent amino acid amide and peptide derivatives

Skalli

Pugnière

et al. 1986

International Journal of Peptide and Protein Research

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Synthesis and Reactions of Oxazolones from L‐Tryptophan and α‐Haloacetic Anhydrides

Bergman

Lidgren

Gogoll

1992

Bulletin des Soc Chimique

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Optically active 5(4/f)-oxazoloncs havc bccn synthcsizcd from L-tryptophan and an cxccss of trifluoro-, Lrichloro-, and dicliloroacctic anhydrides. Some of thc 5(4/f)-oxazolones havc bccn furlhcr uansfonncd to thc isomeric fi(Z/~-oxazoloncs as wcll as oxazoloncs wilh cxocyclic doublc bonds. Trcalmcnt of lhc various oxazoloncs undcr hydrolytic, acidic and Fricdcl-CralLs acylation conditions gavc indole-3-pyruvic acid, a,P-dchydrotrypiophans, j3-carbolincs as wcll as thc functionalizcd cyclopcntanoindolc 32. Trcatmcnt ol the 4-(3-indolylmclhyl)-2-Lrinuoromcdlyl-5(Z//)-ox~olonc (17) with uifluoroacctic acid gavc Ui c 3,4-bridgcd azcpinoindolc 35.Introduction:

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Aromatization of 3,4-dihydro-β-carboline-3-qarboxylic acid and its derivatives through a carbanion intermediate : mechanistic study and use in chemical synthesis

Cited by 13 publications

References 8 publications

Reactivity of β‐Carbolines and Cyclopenta[b]indolones Prepared from the Intramolecular Cyclization of 5(4H)‐Oxazolones Derived from L‐Tryptophan

Reactivity of β‐Carbolines and Cyclopenta[b]indolones Prepared from the Intramolecular Cyclization of 5(4H)‐Oxazolones Derived from L‐Tryptophan

Chymotrypsin catalysed synthesis of fluorescent amino acid amide and peptide derivatives

Synthesis and Reactions of Oxazolones from L‐Tryptophan and α‐Haloacetic Anhydrides

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