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Study of the reactivity of ketone enolates with 3‐halo‐2‐amino derivatives of benzo[ b ]thiophene under photostimulated s RN 1 reaction conditions
Author(s) -
Beltran Lluís,
Gálvez Carmen,
Prats Montserrat,
Salgado Juan
Publication year - 1992
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.5570290438
Subject(s) - chemistry , thiophene , reactivity (psychology) , ketone , substrate (aquarium) , medicinal chemistry , substitution reaction , reagent , organic chemistry , stereochemistry , medicine , oceanography , alternative medicine , pathology , geology
Reactivity of the 3‐halo‐2‐amino derivatives of benzo[6]thiophene 1a‐c and 2 with several ketone enolates 3–5 have been studied under photostimulated S RN 1 reaction conditions. The normal substitution product 6 only was obtained in low yields using potassioacetophenone 3 as the enolate ion and 2‐( tert ‐butoxycarbonylamino)‐3‐chlorobenzo[ b ]thiophene ( 1a ) and 2‐( tert ‐butoxycarbonylamino)‐3‐iodobenzo[ b ]thiophene ( 1c ) as substrates. In all reactions the main product was the corresponding dehalogenated substrate 7a‐b , thus indicating that reduction of the substrate strongly competes with the desired substitution reaction.