A three-component synthesis of (1,3-oxazol-2-yl)-1,2-dihydro(iso)quinoline and its further structural diversifications
2005
Abstract
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)]
Details
Title
A three-component synthesis of (1,3-oxazol-2-yl)-1,2-dihydro(iso)quinoline and its further structural diversifications
Author(s)
Tron, Gian Cesare ; Zhu, Jieping
Published in
Synlett
Issue
3
Pages
532-534
Date
2005
ISSN
0936-5214
Keywords
Esters Role: RCT (Reactant); RACT (Reactant or reagent) (chloroformates; prepn. of isoxazoles via Reissert-type three-component coupling reaction of isoquinolines or quinolines with chloroformates and morpholinyl-alpha -isocyano-beta -phenylpropionamide); Coupling reaction (three-component; Reissert; prepn. of isoxazoles via Reissert-type three-component coupling reaction of isoquinolines or quinolines with chloroformates and morpholinyl-alpha -isocyano-beta -phenylpropionamide); isocyanopropanamide isoquinoline chloroformate Reissert three component coupling; substituted isoxazole prepn; furan prepn
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
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)
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
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
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
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Published
Peer-reviewed publications
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Record creation date
2010-11-25