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Studies on ketene and its derivatives. LXXXIII . Reaction of diketene with isoquinolinium and pyridinium methylide derivatives
Author(s) -
Kato Tetsuzo,
Chiba Takuo,
Tanaka Shigeru
Publication year - 1976
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.5570130308
Subject(s) - diketene , chemistry , isoquinoline , ketene , pyridinium , medicinal chemistry , organic chemistry
Reaction of isoquinolinium bis(ethoxycarbonyl)methylide (I) with diketene gave diethyl 1‐acetyl‐2,3‐dihydro‐2‐oxopyrrolo[2,1‐α]isoquinoline‐3,3‐dicarboxylate (VI), which on hydrolysis with dilute hydrochloric acid afforded ethyl 1‐acetyl‐2‐hydroxypyrrolo[2,1‐α]isoquinoline‐3‐carboxylate (IX) and ethyl 3‐methylpyrrolo[2,1‐α]isoquinoline‐3‐carboxylate (X). On the other hand, isoquinolinium cyanoethoxycarbonylmethylide (IIa) reacted with diketene to give isoquinolinium cyano(3‐ethoxycarbonyloxy‐3‐butenoyl)methylide (XIIIa) which was isomerized to isoquinolinium cyano(3‐ethoxycarbonyloxy‐2‐butenoyl)methylide (XIII). Similarly, reactions of isoquinolinium cyanomethoxycarbonylmethylide (IIb) and pyridinium cyanoalkoxycarbonyl‐methylide (IIIa,b) with diketene gave rise to the corresponding cyano(3‐alkoxycarbonyloxy‐3‐butenoyl)methylides (XIIb, XVIa,b).