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Tandem one-pot synthesis of polysubstituted pyridines using the Blaise reaction intermediate and 1,3-enynes.
Org Lett. 2011 Dec 16; 13(24):6390-3.OL

Abstract

A tandem one-pot method for the construction of a pyridine moiety with selective control of substitution patterns has been developed through the sequential reactions of nitrile with a Reformatsky reagent and 1,3-enyne involving regio- and chemoselective addition of the Blaise reaction intermediate to 1,3-enyne, followed by isomerization, cyclization, and an aromatization cascade.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chun YS
Department of Chemistry and Nano Science (BK21), Ewha Womans University, Seoul 120-750, Korea.
Lee JH
No affiliation info available
Kim JH
No affiliation info available
Ko YO
No affiliation info available
Lee SG
No affiliation info available

MeSH

AlkynesCyclizationMolecular StructureNitrilesPyridinesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22074496

Citation

Chun, Yu Sung, et al. "Tandem One-pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-enynes." Organic Letters, vol. 13, no. 24, 2011, pp. 6390-3.
Chun YS, Lee JH, Kim JH, et al. Tandem one-pot synthesis of polysubstituted pyridines using the Blaise reaction intermediate and 1,3-enynes. Org Lett. 2011;13(24):6390-3.
Chun, Y. S., Lee, J. H., Kim, J. H., Ko, Y. O., & Lee, S. G. (2011). Tandem one-pot synthesis of polysubstituted pyridines using the Blaise reaction intermediate and 1,3-enynes. Organic Letters, 13(24), 6390-3. https://doi.org/10.1021/ol202691b
Chun YS, et al. Tandem One-pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-enynes. Org Lett. 2011 Dec 16;13(24):6390-3. PubMed PMID: 22074496.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tandem one-pot synthesis of polysubstituted pyridines using the Blaise reaction intermediate and 1,3-enynes. AU - Chun,Yu Sung, AU - Lee,Jun Hee, AU - Kim,Ju Hyun, AU - Ko,Young Ok, AU - Lee,Sang-gi, Y1 - 2011/11/10/ PY - 2011/11/15/entrez PY - 2011/11/15/pubmed PY - 2012/2/22/medline SP - 6390 EP - 3 JF - Organic letters JO - Org Lett VL - 13 IS - 24 N2 - A tandem one-pot method for the construction of a pyridine moiety with selective control of substitution patterns has been developed through the sequential reactions of nitrile with a Reformatsky reagent and 1,3-enyne involving regio- and chemoselective addition of the Blaise reaction intermediate to 1,3-enyne, followed by isomerization, cyclization, and an aromatization cascade. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22074496/Tandem_one_pot_synthesis_of_polysubstituted_pyridines_using_the_Blaise_reaction_intermediate_and_13_enynes_ L2 - https://doi.org/10.1021/ol202691b DB - PRIME DP - Unbound Medicine ER -