Pseudo-intramolecular Cyclization of α-Nitro-δ-keto Nitrile Leading to 2-Amino-3-nitro-1,4-dihydropyridines
A novel concept—the pseudo-intramolecular process—is applied to the synthesis of multiply functionalized heterocyclic compounds. Acidic α-nitro-δ-keto nitrile easily forms an ammonium salt upon treatment with an amine. When the amine is liberated under equilibrium, an intimate pair, namely, a nucleo...
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| Published in: | Chemistry letters Vol. 38; no. 7; pp. 680 - 681 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
The Chemical Society of Japan
2009
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| Online Access: | Get full text |
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| Summary: | A novel concept—the pseudo-intramolecular process—is applied to the synthesis of multiply functionalized heterocyclic compounds. Acidic α-nitro-δ-keto nitrile easily forms an ammonium salt upon treatment with an amine. When the amine is liberated under equilibrium, an intimate pair, namely, a nucleophilic amine and an electrophilic keto nitrile are located close to each other, is formed; thus the amine efficiently attacks a cyano group of keto nitrile. As a result of subsequent cyclization, 1,4-dihydropyridines containing an amino and a nitro group at the vicinal positions as a partial structure are afforded. |
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| ISSN: | 0366-7022 1348-0715 |
| DOI: | 10.1246/cl.2009.680 |