Practical Syntheses of Functionalized 1-Oxo-L,2,3,4-Tetrahydro-β-carboline-3-carboxylic Acid Esters

Jeannin, Laurent; Sápi, János; Vassileva, Elka; Renard, Pierre; Laronze, Jean‐Yves

doi:10.1080/00397919608002610

Cited by 10 publications

(5 citation statements)

References 6 publications

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“…Previous reports on the synthesis of compounds 5b − d involve (1) the ring closure of isocyanates or isothiocyanates with polyphosphoric acid (PPA; for 5c , d ), ,, trifluoroacetic acid (TFA; for 5b ), a mixture of HBr and HOAc (for 5b ), and AlCl 3 (for 5b ), (2) cyclization of phenethylcarbamates with PPA (for 5c , d ) , and a mixture of P 2 O 5 and POCl 3 (for 5c ), , and (3) Bischler−Napieralski reactions from ortho-substituted N -acyl-2-phenethylamines , and subsequent reduction of the imide formed (for 5c ). None of these methods have been successfully applied to the preparation of the three lactams, and in most cases, yields are from low to moderate and several steps are involved in the synthesis.…”

Section: Resultsmentioning

confidence: 99%

Insertion of Isocyanides, Isothiocyanates, and Carbon Monoxide into the Pd−C Bond of Cyclopalladated Complexes Containing Primary Arylalkylamines of Biological and Pharmaceutical Significance. Synthesis of Lactams and Cyclic Amidinium Salts Related to the Isoquinoline, Benzo[g]isoquinoline, and β-Carboline Nuclei

et al. 2008

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Cyclometalation of 3-(2-naphthyl)-d-alanine methyl ester is achieved by reacting the corresponding hydrochloride salt and Pd(OAc)2 in a 1:1 molar ratio (acetonitrile, room temperature, 6 days). Although the chloro-bridged dimer (A) cannot be isolated in a pure form, addition of RNC to the reaction mixture affords the mononuclear derivatives (R)-[Pd{κ2(C,N)-C10H6CH2CH(CO2Me)NH2-2}Cl(CNR)] (R = tBu (1a- t Bu), Xy (C6H3Me2-2,6) (1a-Xy)). Similar complexes (S)-[Pd{κ2(C,N)-C8H5N(CH2CH(CO2Me)NH2)-2}Cl(CNR)] (R = tBu (1b- t Bu), Xy (1b-Xy)) are prepared from RNC and a previously reported cyclometalated derivative of l-tryptophan methyl ester, (S,S)-[Pd2{κ2(C,N)-C8H5N(CH2CH(CO2Me)NH2)-2}2(μ-Cl)2] (B). Compound 1b-Xy reacts with XyNC to give the iminoacyl complex (S)-[Pd{κ2(C,N)-C(NXy)C8H5N(CH2CH(CO2Me)NH2)-2}Cl(CNXy)] (2b), whose crystal structure has been determined by X-ray diffraction studies. The cyclopalladated dimer B or those containing phenethylamine (C) or phentermine (D; see Chart ) reacts with RNC (R = tBu, Xy) in refluxing chloroform or toluene to render, depending on the reaction conditions, the cyclic amidines (3c- t Bu, 3d-Xy) or the amidinium salts (4b- t Bu, 4c- t Bu, 4c-Xy, 4d- t Bu, 4d-Xy). The amidines 3a- t Bu and 3a-Xy and the amidinium salts 4a- t Bu and 4a-Xy are synthesized from complexes 1a- t Bu and 1a-Xy. When D reacts with isothiocyanates RNCS (R = Me, To (C6H4Me-4)), the cyclic amidinium salts 4d-Me and 4d-To are isolated. Amidinium triflates derived from phentermine with an aryl substituent at the exocyclic nitrogen atom (4d-Xy, 4d-To) present E/Z isomerism in CHCl3 or CH2Cl2 solution. CO reacts with A−D to give, after depalladation, the corresponding lactams: (R)-1-oxo-3-(methoxycarbonyl)-1,2,3,4-tetrahydrobenzo[g]isoquinoline (5a), (S)-1-oxo-3-(methoxycarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (5b), 1-oxo-1,2,3,4-tetrahydroisoquinoline (5c), and 1-oxo-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (5d). The crystal structures of compounds 4b- t Bu, 4c- t Bu, 4d- t Bu, 4d-Xy, 4d-Me, 4d-To, and 5a−d have been determined by X-ray diffraction studies.

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Section: Resultsmentioning

confidence: 99%

Insertion of Isocyanides, Isothiocyanates, and Carbon Monoxide into the Pd−C Bond of Cyclopalladated Complexes Containing Primary Arylalkylamines of Biological and Pharmaceutical Significance. Synthesis of Lactams and Cyclic Amidinium Salts Related to the Isoquinoline, Benzo[g]isoquinoline, and β-Carboline Nuclei

et al. 2008

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“…1-Oxo-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid ester 15 (R:H) core, which is considered as a rigid pseudopeptide analogue of tryptophan, could be a valuable scaffold for the synthesis of diverse highly functionalized tri-, tetra(poly)cyclic systems of biological interest. For a structure-activity relationship study, a tandem acylazide (12) formation-Curtius rearrangement-acid catalysed cyclisation process proved to be efficient, providing 4-substituted 1-oxotetrahydro-b-carboline derivatives 15 in 40-68% overall yield [21] (Fig. 5).…”

Section: Synthesis Of Functionalized Constrained Tricyclic Tryptophan...mentioning

confidence: 99%

Multicomponent Approach for the Synthesis of Non‐Natural Tryptophan, Tryptamine and β‐Carboline Derivatives

et al. 2004

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Organic chemistryOrganic chemistry Z 0200 Multicomponent Approach for the Synthesis of Non-Natural Tryptophan, Tryptamine and β-Carboline Derivatives -[33 refs.]. -(JEANNIN, L.; BOISBRUN, M.; NEMES, C.; COCHARD, F.; LARONZE, M.; DARDENNES, E.; KOVACS-KULYASSA, A.; SAPI, J.; LARONZE, J.-Y.; C. R. Chim. 6 (2003) 5-6, 517-528; Fac. Pharm., CNRS, Univ. Reims-Champagne-Ardenne, F-51096 Reims, Fr.; Eng.) -Lindner 22-277

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“…32 The 1-Oxo-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid ester 47 (R:H) core is considered as a rigid pseudopeptide analog of tryptophan and could represent a valuable scaffold for the synthesis of futher functionalized polycyclic systems of biological interest.…”

Section: Scheme 13mentioning

confidence: 99%