Bohlmann-Rahtz Cyclodehydration of Aminodienones to Pyridines Using N-Iodosuccinimide
Abstract
:1. Introduction
2. Results and Discussion
Entry | 1 | 2 | 3 | Yield% a | 4 | Yield% b |
---|---|---|---|---|---|---|
1 | 1a | 2a | | 3aa (82) | | 4aa (66 or 84c) |
2 | 1b | 2a | | 3ba (23) | | 4ba (>98) |
3 | 1a | 2b | | 3ab (85) | | 4ab (>98)d |
4 | 1a | 2c | | 3ac (86) | | 4ac (97) |
5 | 1a | 2d | | 3ad (95) | | 4ad (>98) |
6 | 1c | 2a | | 3ca (68) | | 4ca (>98)e |
3. Experimental Section
3.1. General
3.2. Typical experimental procedures
3.2.1. Typical procedure for Michael addition of an enamine 1 and ethynyl ketone 2
3.2.2. Typical procedure for cyclodehydration of a Bohlmann-Rahtz aminodienone 3 using NIS
3.2.3. Typical procedure for the synthesis of propargylic alcohols 9 from aldehydes 10
3.3. Experimental procedures
3.3.1. Ethyl 3-amino-3-phenylpropenoate (1b)
3.3.2. tert-Butyl β-aminocrotonate (1c)
3.3.3. 1-Phenylprop-2-yn-1-one (2b)
3.3.4. 1-(4-Chlorophenyl)prop-2-yn-1-one (2c)
3.3.5. 1-(4-Methoxyphenyl)prop-2-yn-1-one (2d)
3.3.6. (2Z,4E)-2-Amino-3-ethoxycarbonylheptadien-6-one (3aa)
3.3.7. (2Z,4E)-2-Amino-3-ethoxycarbonyl-1-phenylhexadien-6-one (3ba)
3.3.8. (2Z,4E)-2-Amino-3-ethoxycarbonyl-6-phenylhexadien-6-one (3ab)
3.3.9. (2Z,4E)-2-Amino-3-ethoxycarbonyl-6-(4-chlorophenyl)hexadien-6-one (3ac)
3.3.10. (2Z,4E)-2-Amino-3-ethoxycarbonyl-6-(4-methoxyphenyl)hexadien-6-one (3ad)
3.3.11. (2Z,4E)-2-Amino-3-tert-butoxycarbonylheptadien-6-one (3ca)
3.3.12. Ethyl 2,6-dimethylpyridine-3-carboxylate (4aa)
3.3.13. Ethyl 6-methyl-2-phenylpyridine-3-carboxylate (4ba)
3.3.14. Ethyl 2-methyl-6-phenylpyridine-3-carboxylate (4ab)
3.3.15. Ethyl 2-methyl-6-(4-chlorophenyl)pyridine-3-carboxylate (4ac)
3.3.16. Ethyl 2-methyl-6-(4-methoxyphenyl)pyridine-3-carboxylate (4ad)
3.3.17. tert-Butyl 2,6-dimethylpyridine-3-carboxylate (4ca)
4. Conclusions
Acknowledgements
References and Notes
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Bagley, M.C.; Glover, C. Bohlmann-Rahtz Cyclodehydration of Aminodienones to Pyridines Using N-Iodosuccinimide. Molecules 2010, 15, 3211-3227. https://doi.org/10.3390/molecules15053211
Bagley MC, Glover C. Bohlmann-Rahtz Cyclodehydration of Aminodienones to Pyridines Using N-Iodosuccinimide. Molecules. 2010; 15(5):3211-3227. https://doi.org/10.3390/molecules15053211
Chicago/Turabian StyleBagley, Mark C., and Christian Glover. 2010. "Bohlmann-Rahtz Cyclodehydration of Aminodienones to Pyridines Using N-Iodosuccinimide" Molecules 15, no. 5: 3211-3227. https://doi.org/10.3390/molecules15053211