The Prins Cascade Cyclization Reaction for the Synthesis of Angularly‐Fused Tetrahydropyran and Piperidine Derivatives | Zendy

Subba Reddy B. V. | Zendy; Kumar Harish | Zendy; Borkar Prashant | Zendy; Yadav J. S. | Zendy; Sridhar B. | Zendy

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The Prins Cascade Cyclization Reaction for the Synthesis of Angularly‐Fused Tetrahydropyran and Piperidine Derivatives

Author(s) -

Subba Reddy B. V.,

Kumar Harish,

Borkar Prashant,

Yadav J. S.,

Sridhar B.

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201201387

Subject(s) - chemistry , tetrahydropyran , isoquinoline , prins reaction , piperidine , amine gas treating , selectivity , medicinal chemistry , cascade , stereochemistry , organic chemistry , ring (chemistry) , catalysis , chromatography

2‐Arylethylbut‐3‐en‐1‐ol is found to undergo smooth Prins cascade reactions with various aldehydes in the presence of Sc(OTf) 3 (10 mol‐%) and a stoichiometric amount of TsOH to afford the corresponding trans ‐fused hexahydro‐1 H ‐benzo[ f ]isochromenes in good yields with excellent selectivity. Likewise, N ‐tosyl‐2‐phenethylbut‐3‐en‐1‐amine gives trans ‐fused octahydrobenzo[ f ]isoquinoline derivatives under similar conditions. This is the first example of the synthesis of hexahydro‐1 H ‐benzo[ f ]isochromene and octahydrobenzo‐[ f ]isoquinoline from 2‐arylethylbut‐3‐en‐1‐ol and N ‐tosyl‐2‐phenethylbut‐3‐en‐1‐amine, respectively.

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