TY - JOUR
T1 - Synthesis of cyclic analogues of hexamethylenebis(3-pyridine)amide (HMBPA) in a one-pot process
AU - Zamudio-Medina, Angel
AU - García-González, Ma Carmen
AU - Gutierrez-Carrillo, Atilano
AU - González-Zamora, Eduardo
N1 - Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.
PY - 2015/1/21
Y1 - 2015/1/21
N2 - A series of cyclic analogues of hexamethylenebis(3-pyridine)amide was prepared based upon a Ugi-3CR and aza-Diels-Alder reaction as a post-functionalization in a one-pot process. A simple condensation of commercially available diamine and aldehydes followed by isonitrile α-addition provides the oxazole intermediates, finally an aza-Diels-Alder cycloaddition and ring-opening using maleic anhydride provides the desired compounds in modest overall yields in approximately 40 min using microwaves as the heat source and scandium(III) triflate as a catalyst.
AB - A series of cyclic analogues of hexamethylenebis(3-pyridine)amide was prepared based upon a Ugi-3CR and aza-Diels-Alder reaction as a post-functionalization in a one-pot process. A simple condensation of commercially available diamine and aldehydes followed by isonitrile α-addition provides the oxazole intermediates, finally an aza-Diels-Alder cycloaddition and ring-opening using maleic anhydride provides the desired compounds in modest overall yields in approximately 40 min using microwaves as the heat source and scandium(III) triflate as a catalyst.
KW - Cycloaddition
KW - Heteroatom
KW - Heterocycles
KW - Immonium (iminium) ion reactions
KW - Synthetic organic
UR - http://www.scopus.com/inward/record.url?scp=84920164855&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2014.12.018
DO - 10.1016/j.tetlet.2014.12.018
M3 - Artículo
AN - SCOPUS:84920164855
SN - 0040-4039
VL - 56
SP - 627
EP - 629
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 4
ER -