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Please login to access the full content or check if you have access via1.2.1.2 Third Component 1,3-Dicarbonyl Compound (with Ammonia or Amines: Hantzsch Pyridine Synthesis)
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Vanden Eynde, J. J.; Mayence, A., Science of Synthesis: Multicomponent Reactions, (2014) 1, 67.
General Introduction
Derivatives of the 1,4-dihydropyridine-3,5-dicarboxylic acid skeleton and structurally related analogues are widely known under the name of Hantzsch 1,4-dihydropyridines or the 1,4-DHP abbreviation. It was at the end of the 19th century that Arthur Hantzsch had the idea to heat a mixture of acetaldehyde, ammonia, and ethyl 3-oxobutanoate in the absence of solvent. The compound so-obtained was identified as diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1) (Scheme 1). A first report on the experiment appeared in 1881[1] and it was followed, 1 year later, by the habilitation thesis of Hantzsch published in Justus Liebigs Annalen der Chemie.[2] The reaction is now named the “Hantzsch pyridine synthesis”, although the products are in fact dihydropyridines.
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M8 | M8 | Meeee (%) | Mee |
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8-eeeeeee | Me | 88 | [8] |
8-eeeee | Me | 88 | [8] |
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8-eeeee | e-Me | 88 | [8] |
8-eeeeeee | Me | 88 | [8] |
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8-Mee | Me | 88 | [8] |
8-M8MM8M8 | Me | 88 | [8] |
8-M8MM8M8 | Me | 88 | [8] |
8-M8MM8M8 | e-Me | 88 | [8] |
8-M8MM8M8 | Me | 88 | [8] |
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8-MeM8M8 | e-Me | 88 | [8] |
8-MeMM8M8 | Me | 88 | [8] |
8-MMM8M8 | Me | 88 | [8] |
8-M8MM8M8 | Me | 88 | [8] |
8-MM8MM8M8 | Me | 88 | [8] |
8-Me8MM8M8 | Me | 88 | [8] |
Mee | Me | 8 | [8] |
8,8-Me8M8M8 | Me | 88 | [8] |
Me | 88 | [8] | |
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8-eeeeeeee | Me | 88 | [8] |
8-eeeeeeee | Me | 88 | [8] |
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References
[1] | Meeeeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[2] | Meeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 8. |
[3] | Meee, M.; Meeeeee, M. M.; Meeeee, M. M.; Meeeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 888. |
[4] | Meeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeee, M., Meeeeee.-Meeeee., (8888) 88, 888. |
[5] | Meeeeee, M.; Meeee, M., Mee. Mee. Mee., (8888) 8, 888. |
[6] | Meeeee, M.; Meeeeee, M.-M., Meeeee Meeeeeeeeeee, 8ee ee., Meeee: Meeee, (8888); e 888. |
[7] | Meeee, M.; Meeeeeee, M., Meéeeeee, (8888) 88, 888. |
[8] | Meeeeee, M.; eee Meeeeeeee, M., Me Meee Meeeeeee eee Meeee: Meeeeeeeeeeee Meeeeeee ee Meeeeeee Meeeeeeeeeee, 8ee ee., eee Meeeee, M. M.; Meeeeee, M.; Meeeeee, M. M., Mee.; MMM: Meeeeeeee, (8888); ee 888–888. |
[9] | Meeee Meee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeee, M.; Múñee-Meeeeee, M. M.; Meeeeee, M. M.; Meeeá, M.; Meeee, M.; Mee Meeeeeeee, M., Meeeeeeeeee Meeeeee. Meeeeee. Meee M: Meeeeeeee., Meeeeee. Meeeeeeeee., (8888) 888, 888. |
[10] | Meeeãe, M. M.; Meeeee, M. M.; Meeeeee, M. M., Meeeee. Mee. Meee., (8888) 88, 8888. |
[11] | Meeee, M.; Meeeee, M.; Meeeeeeee, M.; Meee, M.; Meeeee, M. M., Meeeee. Mee. Meee., (8888) 8, 8888. |
[12] | Meeeee, M.; Meee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
[13] | Meeeeeeee, M. M.; Meeeee, M. M.; Meeee, M.; Meeee, M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M.; Meeee, M.; Mee, M.; Meeéeee-Míee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeeee, M. M.; Mee, M.; Meeeeee, M. M.; Meeeeeee, M.; Me Meeeeee, M.; Meeeee, M. M.; Meeeeee, M.; MeMeeeee, M. M.; Meeeee, M.; Meeeee-Meeeeeee, M.; Meeeee, M.; Meeeeeeee, M. M.; MeMeee, M. M.; Meeeeeee, M. M.; Meee, M. M.; Meee, M. M.; Meeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Mee Meeeeee, M. M.; Meeee, M. M.; Mee, M. M., Meeeee (Meeeee), (8888) 888, 888. |
[14] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M.; Meeeee, M. M., Mee. M. Mee. Meee., (8888) 88, 8888. |
[15] | Meeeeeeee, M., Me Meeeeeee-Meeee Meee Meeeeeeee, Meeeeee, M.; Meeeeeee, M. M., Mee.; Meeee-MMM: Meeeeeee, Meeeeee, (8888); ee 888–888. |
[19] | Mee, M.-M., Meee.–Meeee M., (8888) 8, 888. |
[20] | Me, M.; Mee, M. M.; Mee, M., Mee. Meeee. Meeee., (8888) 888, 88. |