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Silicon‐Assisted Ethoxycarbonylmethylation of N ‐Methylquinolinium and Isoquinolinium Iodides
Author(s) -
Diaba Faïza,
Le Houerou Cyril,
GrigDubois Micheline,
Rezzonico Bernadette,
Gerval Pierre
Publication year - 2000
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 - 10.1002/1099-0690(200008)2000:16<2915::aid-ejoc2915>3.0.co;2-b
Subject(s) - chemistry , carbanion , regioselectivity , methylene , medicinal chemistry , structural isomer , adduct , fluoride , organic chemistry , catalysis , inorganic chemistry
A new regioselective route to 2‐ethoxycarbonylmethyl‐1,2‐dihydro‐ N ‐methylquinolines and 1‐ethoxycarbonylmethyl‐1,2‐dihydro‐ N ‐methylisoquinolines is described starting from methylquinolinium or ‐isoquinolinium iodides and commercially available ethyltrimethylsilyl acetate (ETSA). The methylene carbanion was generated by fluorodesilylation using caesium fluoride. On exposure to air, the ethoxycarbonylmethyl adducts were oxidised, leading to the corresponding alkylidene derivatives 4 and 5, whereas 2a in solution led slowly to its regioisomer 6a.