TY - JOUR
T1 - Studies on the petasis reaction of 2-pyridinecarbaldehyde derivatives and its products
AU - Mandai, Hiroki
AU - Murota, Kyouta
AU - Suga, Seiji
N1 - Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
PY - 2012
Y1 - 2012
N2 - The Petasis reaction of various 2-pyridinecarbaldehydes with secondary amines and boronic acids in refluxed acetonitrile proceeded to afford desired products up to 96% yield. The reaction proceeded under mild conditions to afford wide range of amines adjacent to heteroaromatic rings. Interestingly, the aldehyde possessing a nucleophilic moiety, 4-(dimethylamino)-2- pyridinecarbaldehyde, with (S)-(-)-N-methyl-1-phenylethylamine and 2 equivalent of trans-2-phenylvinylboronic acid afforded unexpected product, (E)-N-benzyl-3-phenyl-1-(pyridin-2-yl)prop-2-en-1-amine, in high yield. This product might be formed through the direct alkylation of aldehyde by trans-2-phenylvinylboronic acid, followed by anion/enolate isomerization. Derivatization of the Petasis products were also employed and 2-alkyl substituted pyridine derivatives can be obtained through deamination of the Petasis products under the simple hydrogenation conditions.
AB - The Petasis reaction of various 2-pyridinecarbaldehydes with secondary amines and boronic acids in refluxed acetonitrile proceeded to afford desired products up to 96% yield. The reaction proceeded under mild conditions to afford wide range of amines adjacent to heteroaromatic rings. Interestingly, the aldehyde possessing a nucleophilic moiety, 4-(dimethylamino)-2- pyridinecarbaldehyde, with (S)-(-)-N-methyl-1-phenylethylamine and 2 equivalent of trans-2-phenylvinylboronic acid afforded unexpected product, (E)-N-benzyl-3-phenyl-1-(pyridin-2-yl)prop-2-en-1-amine, in high yield. This product might be formed through the direct alkylation of aldehyde by trans-2-phenylvinylboronic acid, followed by anion/enolate isomerization. Derivatization of the Petasis products were also employed and 2-alkyl substituted pyridine derivatives can be obtained through deamination of the Petasis products under the simple hydrogenation conditions.
UR - http://www.scopus.com/inward/record.url?scp=84864131063&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84864131063&partnerID=8YFLogxK
U2 - 10.3987/COM-12-12500
DO - 10.3987/COM-12-12500
M3 - Article
AN - SCOPUS:84864131063
VL - 85
SP - 1655
EP - 1669
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 7
ER -