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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.

| S-EPMC3089121 | biostudies-literature

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

Project description:In the title salt, C7H8N3 (+)·BF4 (-), the 1,2,4-triazolo[4,3-a]pyridinium cation is planar [maximum deviation of 0.016?(2)?Å for all non-H atoms]. The cation and anion constitute a tight ionic pair with an F?N [2.911?(4)?Å] inter-molecular attractive inter-action. The ionic pairs form dimers via stacking inter-actions between inversion-related cations, the normal distance between the cation planes being 3.376?(5)?Å. The dimers are packed in stacks along the a axis and linked via C-H?F hydrogen bond, forming a three-dimensional network.

| S-EPMC3772483 | biostudies-literature

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

Project description:A novel phosphine-catalyzed intermolecular cyclization between 2-sulfonamidobenzaldehyes and ynones is reported. This methodology serves as a conduit for the construction of benzo[ b]azepin-3-ones in good to excellent yields under mild conditions. The resulting 2-benzylidene moieties are formed exclusively in the E-configuration. Mechanistically, this unusual annulation occurs through a phosphine-catalyzed ?-umpolung addition, followed by an aldol reaction. One of the benzo[ b]azepin-3-one products was converted to the core structure of 3-amino-[ a]benzazepin-2-one-1-alkanoic acids, many of which function as angiotensin-converting enzyme inhibitors.

| S-EPMC7338222 | biostudies-literature

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

Project description:The organocatalytic asymmetric synthesis of functionalized 1,3,5-triarylpyrrolidin-2-ones bearing three contiguous stereocenters through an aza-Michael/aldol domino reaction of ?-ketoamides with ?,?-unsaturated aldehydes is described. The domino products were further derivatized by aldehyde olefination under one-pot conditions. The reaction proceeds with excellent diastereoselectivities (>20:1) and good to excellent enantioselectivities (60-96% ee).

| S-EPMC4178285 | biostudies-other

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.

| S-EPMC3344014 | biostudies-literature

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.

| S-EPMC3648246 | biostudies-literature

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.

Project description:An efficient tandem intermolecular one-pot aldol condensation/aza-addition reaction of 2-methyl-3-carbamoylpyrroles and aldehydes was developed for the synthesis of 2,3,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-ones. The reaction proceeded using only 3.0 equiv of ammonium acetate promoter in green solvent poly(ethylene glycol)-400 at 100 °C to afford a series of pyrrolo[3,2-c]pyridinone derivatives in good to excellent yields.

| S-EPMC6645481 | biostudies-literature

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.

| S-EPMC3011526 | biostudies-other

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

Project description:In the title thienopyridine derivative, C(20)H(25)N(3)O(3)S(2), the piperazine ring exhibits a chair conformation and the tetra-hydro-pyridine ring exhibits a half-chair conformation. The folded conformation of the mol-ecule is defined by the N-C-C-N torsion angle of -70.20?(2) °. Inter-molecular C-H?S and C-H?O hydrogen bonds help to establish the packing.

| S-EPMC3213574 | biostudies-literature

Angular Regioselectivity in the Reactions of 2-Thioxopyrimidin-4-ones and Hydrazonoyl Chlorides: Synthesis of Novel Stereoisomeric Octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones.

Project description:The regioselective synthesis of cis and trans stereoisomers of variously functionalized octahydro[1,2,4]triazolo[4,3-a]quinazolin-5-ones was performed. The 2-thioxopyrimidin-4-ones used in the synthesis reacted with hydrazonoyl chlorides in a regioselective manner to produce the angular regioisomers [1,2,4]triazolo[4,3-a]quinazolin-5-ones rather than the linear isomers [1,2,4]triazolo[4,3-a]quinazolin-5-ones. The synthesis process took place with electronic control. The angular regiochemistry of the products was confirmed by X-ray experiments and two-dimensional NMR studies.

| S-EPMC7730367 | biostudies-literature

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