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Reactivity and stereoselectivity of oxazolopyridines with a ring‐junction nitrogen atom
Author(s) -
Monier Mohamed,
AbdelLatif Doaa,
ElMekabaty Ahmed,
Elattar Khaled M.
Publication year - 2019
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.3727
Subject(s) - chemistry , stereoselectivity , stereocenter , enantiopure drug , alkylation , indole test , reactivity (psychology) , ring (chemistry) , nitrogen atom , stereochemistry , oxazolidine , selectivity , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , medicine , alternative medicine , pathology
The present study demonstrates a synopsis of the scientific researches reported on the different reactions of oxazolo[3,2‐ a ]pyridines, besides the preparation of significant fused heterocycles up till now. The different main sections that described the reactivity of the inspected analogues include stereoselective alkylation, reactions involved oxazolidine ring, synthesis of polycyclic systems, indole alkaloids, and alkyl amines. The stereochemical selectivity of oxazolopiperidone lactams is studied, in which the configuration of the stereocenter C8a and substituents at the C8 and C8a effect on the stereoselectivity. On the other hand, the synthetic consequence of the alkylation products provides diverse routes for the synthesis of substituted enantiopure piperidines that are used for the synthesis of natural products, for example, (−)‐rhazinilam, (+)‐eburnamonine, (+)‐aspidospermidine, indole alkaloids such as dihydrocleavamine, nor‐20‐epiuleine, (+)‐dasycarpidone, (+)‐uleine, indoloquinolizidine, (+)‐dihydrocorynantheine, (−)‐dihydrocorynantheol, and indolizines, eg, octahydroindolizines, monomorine I, (−)‐ S ‐coniceine, and (−)‐ R ‐coniceine.