A three-component synthesis of (1,3-oxazol-2-yl)-1,2-dihydro(iso)quinoline and its further structural diversifications

A Reissert-type three-component synthesis of 1,3-oxazol-2-yl-1,2-dihydro(iso)quinolines, e.g., I, was developed using alpha -isocyano-beta -Ph-propionamide as an isonitrile input. The structure of this multicomponent adduct was further diversified taking advantage of the rich chem. of oxazole. [on SciFinder (R)]


Published in:
Synlett, 3, 532-534
Year:
2005
Keywords:
Note:
CAN 142:411275
28-6
Heterocyclic Compounds (More Than One Hetero Atom)
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche,Universita degli Studi del Piemonte Orientale,Novara,Italy.
Journal
0936-5214
written in English.
762-42-5 (Dimethyl acetylenedicarboxylate) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (methoxycarbonyldihydroisoquinolinyl)morpholinylfurandicarboxylate via Diels-Alder cycloaddn. of benzyl(methoxycarbonyldihydroisoquinolinyl)morpholinyloxazole with acetylenedicarboxylate followed by retro-Diels-Alder reaction); 850403-36-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (methoxycarbonyldihydroisoquinolinyl)morpholinylfurandicarboxylate via Diels-Alder cycloaddn. of benzyl(methoxycarbonyldihydroisoquinolinyl)morpholinyloxazole with acetylenedicarboxylate followed by retro-Diels-Alder reaction); 850403-35-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of [alpha -(morpholinocarbonyl)phenylethyl] methoxycarbonyldihydroisoquinolinecarboxamide via hydrolysis of benzyl(methoxycarbonyldihydroisoquinolinyl)morpholinyloxazole); 91-22-5 (Quinoline); 119-65-3 (Isoquinoline); 607-32-9 (5-Nitroisoquinoline); 1125-80-0 (3-Methylisoquinoline); 1532-97-4 (4-Bromoisoquinoline); 1885-14-9 (Phenyl chloroformate); 2439-04-5 (5-Hydroxyisoquinoline); 5263-87-6 (6-Methoxyquinoline); 28920-43-6 (Fmoc chloride); 85059-48-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of isoxazoles via Reissert-type three-component coupling reaction of isoquinolines or quinolines with chloroformates and morpholinyl-alpha -isocyano-beta -phenylpropionamide); 850403-26-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of isoxazoles via Reissert-type three-component coupling reaction of isoquinolines or quinolines with chloroformates and morpholinyl-alpha -isocyano-beta -phenylpropionamide); 850403-27-9P; 850403-28-0P; 850403-29-1P; 850403-30-4P; 850403-31-5P; 850403-32-6P; 850403-33-7P; 850403-34-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of isoxazoles via Reissert-type three-component coupling reaction of isoquinolines or quinolines with chloroformates and morpholinyl-alpha -isocyano-beta -phenylpropionamide)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


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