Heterosynthesis Using Nitriles: Novel Pyrrolo[2,3-b]pyridines
نویسندگان
چکیده
2-Amino-4-benzoyl-1-arylpyrrole-3-carbonitriles react with arylidene malonodinitriles, β-ketoesters and βdiketones to afford pyrrolo[2,3-b]pyridine derivatives.
منابع مشابه
Diastereoselective Ritter reactions of chiral cyclic N-acyliminium ions: synthesis of pyrido- and pyrrolo[2,3-d]oxazoles and 4-Hydroxy-5-N-acylaminopyrrolidines and 5-hydroxy-6-N-acylaminopiperidines.
Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.
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In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicy...
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The structure of the title compound, C(27)H(29)N(5)O(4)S, displays an intra-molecular N-H⋯O hydrogen bond. The pyrrolo-[2,3-b]pyridine core makes a dihedral angle of 85.5 (4)° with the benzyl residue and a dihedral angle of 89.4 (9)° with the tosyl ring. The nitro group is slightly twisted out of the plane of the planar pyrrolo-pyridine system [(-N-)C-C-N-O torsion angle = -4.61 (18)° and (-NH-...
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The benzyl residue in the title compound, C(21)H(23)N(5)·0.5H(2)O, is oriented at a dihedral angle of 83.8 (3)° towards the 1,6-dihydro-imidazo[4,5-d]pyrrolo-[2,3-b]pyridine system. The piperidine ring adopts a chair conformation with the cis substituents displaying a torsion angle of -45.91 (16)°. In the crystal, mol-ecules are accumulated as racemic dimers by two inter-molecular hydrogen bond...
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It is now established that the thieno[2,3-b]pyridines are a potent class of antiproliferatives. One of the main issues encountered for their clinical application is their low water solubility. In order to improve this, two strategies were pursued. First, a morpholine moiety was tethered to the molecular scaffold by substituting the sulphur atom with nitrogen, resulting in a 1H-pyrrolo[2,3-b]pyr...
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