Preparation and stereochemistry of methyl 3‐(and 4)‐ p ‐chlorothiophenoxy‐1‐methylpiperidine‐4‐(and 3)‐carboxylates, and cyclization to benzothiopyranopyridinones | Zendy

Butt Graeme L. | Zendy; Deady Leslie W. | Zendy; Mackay Maureen F. | Zendy

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Preparation and stereochemistry of methyl 3‐(and 4)‐ p ‐chlorothiophenoxy‐1‐methylpiperidine‐4‐(and 3)‐carboxylates, and cyclization to benzothiopyranopyridinones

Author(s) -

Butt Graeme L.,

Deady Leslie W.,

Mackay Maureen F.

Publication year - 1988

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570250154

Subject(s) - chemistry , chlorobenzene , sulfuric acid , stereochemistry , product (mathematics) , medicinal chemistry , organic chemistry , catalysis , geometry , mathematics

The title piperidines were prepared by (a) methanolysis of the corresponding nitriles and (b) addition of p ‐chlorothiophenol to the appropriate tetrahydropyridines. Three esters were obtained with stereochemistry assigned by nmr analysis: 2 [3(a) SAr, 4(e) CO 2 Me], 5 [4(e) SAr, 3(e) CO 2 Me], 6 [4(a) SAr, 3(e) CO 2 Me]. Compounds 2 and 6 cyclized in 70% sulfuric acid. The product structures were established by X‐ray crystallography and, surprisingly, both had trans‐fused rings. Compound 5 , however, did not cyclize but gave 4‐(methylthio)chlorobenzene as the sole isolated product.

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