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Aldol elaboration of 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-ones, masked precursors to acylpyridones.

ABSTRACT: A core 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine-4-one scaffold is elaborated at C-3(Me) by base-mediated aldol condensation to give new 3-alkenyl-4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine-4-ones, which are masked forms related to the acylpyridone natural products.

SUBMITTER: Jones RC

PROVIDER: S-EPMC3302094 | biostudies-literature |

REPOSITORIES: biostudies-literature

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3-(5-Chloro-naphthalene-1-sulfonamido)-2-(2-hy-droxy-eth-yl)-4,5,6,7-tetra-hydro-2H-pyrazolo-[4,3-c]pyridin-5-ium chloride.

Project description:In the cation of the title compound, C(18)H(20)ClN(4)O(3)S(+)·Cl(-), the tetra-hydro-pyridinium ring assumes a half-chair conformation. The dihedral angle between the pyrazole ring and the naphthalene ring system is 75.19?(6)°. In the crystal, ions are linked into a three-dimensional network by N-H?O, N-H?Cl and O-H?Cl hydrogen bonds and weak ?-? stacking inter-actions with centroid-centroid distances of 3.608?(2)?Å.

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2-Methyl-1,2,4-triazolo[4,3-a]pyridin-2-ium tetra-fluoroborate.

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5-tert-Butyl 3-ethyl 1-isopropyl-4,5,6,7-tetra-hydro-1H-pyrazolo-[4,3-c]pyridine-3,5-dicarboxyl-ate.

Project description:In the title compound, C(17)H(27)N(3)O(4), the six-membered ring adopts a half-chair conformation with the N atom and the adjacent methyl-ene C atom displaced by -0.391 (2) and 0.358 (2) Å, respectively, from the plane of the other four atoms. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions.

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5-(2-Chloro-benz-yl)-4,5,6,7-tetra-hydro-thieno[3,2-c]pyridin-2-yl acetate.

Project description:In the title compound, C(16)H(16)ClNO(2)S, the benzene and thio-phene rings make a dihedral angle of 72.60?(4)°. In the crystal, weak C-H?O inter-actions are observed.

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5-(2-Cyano-benz-yl)-4,5,6,7-tetra-hydro-thieno[3,2-c]pyridin-2-yl acetate.

Project description:In the title mol-ecule, C17H16N2O2S, the tetra-hydro-pyridine ring exhibits a half-chair conformation. The mean planes of the ester chain and benzene ring are twisted by 5.5?(1) and 81.32?(5)°, respectively, from the plane of thio-phene ring. In the crystal, weak C-H?O inter-actions link mol-ecules related by translation along [100] into chains.

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Organocatalytic Asymmetric Synthesis of Functionalized 1,3,5-Triarylpyrrolidin-2-ones via an Aza-Michael/Aldol Domino Reaction.

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Ammonium Acetate-Promoted One-Pot Tandem Aldol Condensation/Aza-Addition Reactions: Synthesis of 2,3,6,7-Tetrahydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-ones.

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2-Chloro-1-(4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-5-yl)ethanone.

Project description:In the title compound, C(9)H(10)ClNOS, the dihedral angle between the planar thio-phene ring and 2-chloro-ethane moiety (r.m.s deviations of 0.003 and 0.015?Å, respectively) is 45.79?(6)°. The tetra-hydro-pyridine ring adopts a half-chair conformation. The crystal packing reveals inter-molecular C-H?O inter-actions.

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Phosphine-Catalyzed α-Umpolung-Aldol Reaction for the Synthesis of Benzo[ b]azapin-3-ones.

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2-[4-(4-Methylphenylsulfonyl)piperazin-1-yl]-1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone.

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