Reaction of phthalic anhydrides with methyl isocyanoacetate: A useful synthesis of 1,2-dihydro-1-oxoisoquinolines
In: Chemical and Pharmaceutical Bulletin, Jg. 27 (1979), S. 1373-1377
Online
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Zugriff:
Nitro-1, 2-dihydro-1-oxoisoquinoline-3-carboxylate compounds (5a, b and 9a, b) were synthesized by the reaction of methyl isocyanoacetate with nitrophthalic anhydrides in the presence of 1, 8-diazabicyclo [5. 4. 0] undec-7-ene (DBU), followed by esterification with diazomethane and hydrolysis with HCl. In these reactions, the methylidenephthalide compound (10) was also obtained by hydrolysis of the oxazole-4-carboxylate compound (8b) due to the presence of the bulky ortho nitro group. Moreover, 1, 2-dihydro-4-hydroxy-1-oxoisoquinoline-3-carboxylic acid (16) was prepared via the oxazole dicarboxylic acid compound (15) in good yield.
Titel: |
Reaction of phthalic anhydrides with methyl isocyanoacetate: A useful synthesis of 1,2-dihydro-1-oxoisoquinolines
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Autor/in / Beteiligte Person: | Suzuki, Mamoru ; Nunami, Kenichi ; Yoneda, Naoto ; Miyoshi, Muneji ; Matsumoto, Kazuo |
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Zeitschrift: | Chemical and Pharmaceutical Bulletin, Jg. 27 (1979), S. 1373-1377 |
Veröffentlichung: | Pharmaceutical Society of Japan, 1979 |
Medientyp: | unknown |
ISSN: | 1347-5223 (print) ; 0009-2363 (print) |
DOI: | 10.1248/cpb.27.1373 |
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