Synthesis of fused heterocycles: 1,2,3,4-tetrahydroisoquinolines and ring homologues via sulphonamidomethylation

Orazi, Orfeo O.; Corral, Renée A.; Giaccio, Héctor

doi:10.1039/p19860001977

Cited by 42 publications

(23 citation statements)

References 2 publications

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“…13,14 N-[((3 0 ,4 0 -Dichlorophenyl)methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin (26) has not yet been reported in literature, but its synthesis was performed in analogy to 25; yield of the final sulfonoamidomethylation step 71%; mp 138. 5 Tables 2 and 3.…”

Section: Methodsmentioning

confidence: 99%

“…The chemical shift standard was internal tetramethylsilane for 1 H and 13 C (υ 0 ppm). Digital resolutions in the 1D NMR spectra were 0.14 Hz/point for 1 H, 0.24 Hz/point for 13 C, pulse angles were ca. 30°, and sample concentrations were 0.095-0.230 M. Signal assignments were assisted by APT (attached-proton test), DEPT, gs-COSY, gs-HMQC, and gs-HMBC experiments using standard Bruker software.…”

Section: Methodsmentioning

confidence: 99%

“…Room temperature 1 H (400.1 MHz) and 13 C (100.6 MHz) NMR measurements were performed on a Bruker Avance DPX-400 spectrometer. The chemical shift standard was internal tetramethylsilane for 1 H and 13 C (υ 0 ppm).…”

Section: Methodsmentioning

confidence: 99%

“…1 -10 N-Aralkylsulfonamides were obtained using several slightly modified classical methods, 11,12 N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and N-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines were synthesized by intramolecular sulfonylamidomethylation of N-aralkylsulfonamides in acid medium. 12,13 Some 1 H NMR of the title compounds -recorded at low-field instruments 13,14 -were partially reported before, but here we present a full 1 H and 13 C NMR signal assignments for the first time.…”

Section: N-aralkylsulfonamides N-sulfonyl-1234-tetrahydroisoquinomentioning

confidence: 95%

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Complete1H and13C NMR spectral assignment ofN-aralkylsulfonamides,N-sulfonyl-1,2,3,4-tetrahydroisoquinolines andN-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines. Conformational analysis ofN-[((3′,4′-dichlorophenyl)methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin

et al. 2005

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The complete and unambiguous assignment of the 1H NMR and 13C NMR spectra of 26 N-aralkylsulfonamides, N-sulfonyl-1,2,3,4-tetrahydroisoquinolines and N-sulfonylbenz[c]azepines was performed on the basis of APT, DEPT, homonuclear (gs-COSY) and 1H-detected heteronuclear one-bond (gs-HMQC) and long-range (gs-HMBC) correlation experiments. The methylated 2,3,4,5-tetrahydro-1H-2-benzazepine derivative 26 adopts a chair conformation as determined by 1H-1H coupling analysis and gamma-gauche effects. This is supported by a single-crystal X-ray structure analysis.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: N-aralkylsulfonamides N-sulfonyl-1234-tetrahydroisoquinomentioning

confidence: 95%

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Complete1H and13C NMR spectral assignment ofN-aralkylsulfonamides,N-sulfonyl-1,2,3,4-tetrahydroisoquinolines andN-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines. Conformational analysis ofN-[((3′,4′-dichlorophenyl)methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin

et al. 2005

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“…También se estudió en nuestro laboratorio la síntesis de 1,2,3,4tetrahidroisoquinolinas (36) y homólogos vía sulfonilamidometilación intramolecular (44) de N-aralquilsulfonamidas (35) como complemento al estudio de la ciclización de las bencil y 2-feniletilsulfonamidas y a las N-(2-feniletil)-p-toluensulfonamidas de Ito y Tanaka. (34) Las sulfonamidas fueron preparadas por reacción de la amina (2-feniletil, 3-fenilpropil y 4-fenilbutilamina) con el correspondiente cloruro de sulfonilo R 2 SO2Cl en benceno-tolueno y en presencia de carbonato de potasio acuoso.…”

Section: Esquema 22unclassified

Sulfonilamidometilación intramolecular de 2-naftilmetan y 2-(2-naftil)etansulfonamidas

Sasiambarrena¹

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Los objetivos principales de este trabajo de tesis son los siguientes: - Sintetizar nuevas 2-naftilmetansulfonamidas y 2-(2-naftil)etansulfonamidas para utilizarlas como sustratos en reacciones de sulfonilamidometilación intramolecular. - Estudiar la reacción de sulfonilamidometilación intramolecular de 2- naftilmetansulfonamidas con formaldehído en medio ácido para la obtención de 2,4-dihidro-1H-nafto[1,2-d]3,2-tiazinas 3,3-dióxido y 3,4-dihidro-1H-nafto[2,3- d]2,3-tiazinas 2,2-dióxido empleando resinas de intercambio iónico Amberlyst XN- 1010 como catalizador ácido. - Estudiar la reacción de sulfonilamidometilación intramolecular de 2-(2- naftil)etansulfonamidas con formaldehído en medio ácido para la obtención de 1,2,4,5-tetrahidronafto[1,2-d]3,2-tiazepinas 3,3-dióxido y 1,2,4,5- tetrahidronafto[2,3-d]3,2-tiazepinas 3,3-dióxido empleando resinas de intercambio iónico Amberlyst XN-1010 como catalizador ácido. - Analizar estructuralmente los productos obtenidos mediante análisis elemental, espectroscopia 1H-RMN, 13C-RMN, RMN bidimensional, FT-IR y espectrometría de masa.

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Isoquinolinols and Their Hydrogenated Derivatives

Hoshino¹,

Hart²,

Umezawa³

1995

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Synthesis of fused heterocycles: 1,2,3,4-tetrahydroisoquinolines and ring homologues via sulphonamidomethylation

Cited by 42 publications

References 2 publications

Complete1H and13C NMR spectral assignment ofN-aralkylsulfonamides,N-sulfonyl-1,2,3,4-tetrahydroisoquinolines andN-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines. Conformational analysis ofN-[((3′,4′-dichlorophenyl)methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin

Complete1H and13C NMR spectral assignment ofN-aralkylsulfonamides,N-sulfonyl-1,2,3,4-tetrahydroisoquinolines andN-sulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepines. Conformational analysis ofN-[((3′,4′-dichlorophenyl)methyl)sulfonyl]-3-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin

Sulfonilamidometilación intramolecular de 2-naftilmetan y 2-(2-naftil)etansulfonamidas

Isoquinolinols and Their Hydrogenated Derivatives

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