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- W2024973025 abstract "The 1-substituted 3-amino-4H-quinolizin-4-ones 13, available in two steps from 10 and methyl (Z)-2-benzyloxycarbonylamino-3-(dimethylamino)propenoate (11), were diazotized to give the stable diazonium tetrafluoroborates 7a and 7b. Heating of these diazonium salts in alcohols gave mixtures of 3-unsubstituted quinolizine derivatives 8a and 8b and the alkyl indolizine-3-carboxylates 9a−h. The ratio of the two types of products 8 and 9 was dependent on the type of alcohol employed. Thus, treatment of 7a or 7b with 2-propanol predominantly resulted in the 3-unsubstituted quinolizinones 8, while treatment of 7a or 7b with primary alcohols gave the indolizine-3-carboxylates 9 as the major products in most cases. The transformation of the 4-oxoquinolizine-3-diazonium tetrafluoroborates 7a and 7b into the alkyl indolizine-3-carboxylates 9a−h represents the first example of a Wolff rearrangement in the fused cyclic α-diazoamide series." @default.
- W2024973025 created "2016-06-24" @default.
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- W2024973025 date "2010-05-22" @default.
- W2024973025 modified "2023-09-26" @default.
- W2024973025 title "ChemInform Abstract: Ring Contractions of 4-Oxoquinolizine-3-diazonium Tetrafluoroborates, by an Aza Wolff Rearrangement, to Alkyl Indolizine-3-carboxylates." @default.
- W2024973025 cites W2950650493 @default.
- W2024973025 doi "https://doi.org/10.1002/chin.200217138" @default.
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