Bohlmann–Rahtz pyridine synthesis

Bohlmann–Rahtz pyridine synthesis
Named after	Ferdinand Bohlmann; Dieter Rahtz
Reaction type	Ring forming reaction
Identifiers
Organic Chemistry Portal	bohlmann-rahtz-pyridine-synthesis

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In organic chemistry, the Bohlmann–Rahtz pyridine synthesis is a reaction that generates substituted pyridines in two steps, first a condensation reaction between an enamine and an ethynylketone to form an aminodiene intermediate, which after heat-induced E/Z isomerization undergoes a cyclodehydration to yield 2,3,6-trisubstituted pyridines.^[1]^[2]^[3]^[4]

References

^ Bagley, Mark C.; Dale, James W.; Bower, Justin (January 2001). "A New Modification of the Bohlmann-Rahtz Pyridine Synthesis". Synlett. 2001 (7): 1149–1151. doi:10.1055/s-2001-15140.
^ Xiong, Xi; Bagley, Mark C.; Chapaneri, Krishna (2 August 2004). "A new mild method for the one-pot synthesis of pyridines". Tetrahedron Letters. 45 (32): 6121–6124. doi:10.1016/j.tetlet.2004.06.061.
^ Bagley, Mark C.; Fusillo, Vincenzo; Jenkins, Robert L.; Lubinu, M. Caterina; Mason, Christopher (2013). "One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor". Beilstein Journal of Organic Chemistry. 9 (1). Beilstein-Institut: 1957–1968. doi:10.3762/bjoc.9.232. PMC 3817555. PMID 24204407.
^ Dohe, Janis; Müller, Thomas J. J. (2016). "Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines". Zeitschrift für Naturforschung B. 71 (6): 705–718. doi:10.1515/znb-2016-0046. S2CID 197153613.

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[1] Bagley, Mark C.; Dale, James W.; Bower, Justin (January 2001). "A New Modification of the Bohlmann-Rahtz Pyridine Synthesis". Synlett. 2001 (7): 1149–1151. doi:10.1055/s-2001-15140.

[2] Xiong, Xi; Bagley, Mark C.; Chapaneri, Krishna (2 August 2004). "A new mild method for the one-pot synthesis of pyridines". Tetrahedron Letters. 45 (32): 6121–6124. doi:10.1016/j.tetlet.2004.06.061.

[3] Bagley, Mark C.; Fusillo, Vincenzo; Jenkins, Robert L.; Lubinu, M. Caterina; Mason, Christopher (2013). "One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor". Beilstein Journal of Organic Chemistry. 9 (1). Beilstein-Institut: 1957–1968. doi:10.3762/bjoc.9.232. PMC 3817555. PMID 24204407.

[4] Dohe, Janis; Müller, Thomas J. J. (2016). "Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines". Zeitschrift für Naturforschung B. 71 (6): 705–718. doi:10.1515/znb-2016-0046. S2CID 197153613.

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