Easy access to medium rings by entropy/strain reduction, Part 3 . Competition between dihydroazepine and enamine formation in reaction of tetrahalosubstituted dibromides with primary amines | Zendy

Walsh James G. | Zendy; Gilheany Declan G. | Zendy

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Easy access to medium rings by entropy/strain reduction, Part 3 . Competition between dihydroazepine and enamine formation in reaction of tetrahalosubstituted dibromides with primary amines

Author(s) -

Walsh James G.,

Gilheany Declan G.

Publication year - 2002

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.5570390624

Subject(s) - chemistry , enamine , potassium carbonate , medicinal chemistry , toluene , benzazepine , stereochemistry , primary (astronomy) , organic chemistry , catalysis , physics , astronomy

The reaction of Z,Z‐2,3,4,5‐tetrahalo‐2,4‐dien‐1,6‐dibromides ( 3 , R 1 ‐ R 4 = Cl, Br) with primary amines in the presence of potassium carbonate leads to both the dihydroazepines 4 and secondary enamines 5 . The formation of enamine is suppressed with toluene sulfonamide as nitrogen source. (2Z,4Z)‐2,3,4,5‐Tetrabromo‐hexa‐2,4‐diene‐1,6‐diol (2, R 1 ‐ R 4 = Br) is atropisomeric in solution.

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