TY - JOUR
T1 - Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines
T2 - One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones
AU - Giustiniano, Mariateresa
AU - Mercalli, Valentina
AU - Amato, Jussara
AU - Novellino, Ettore
AU - Tron, Gian Cesare
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/7/14
Y1 - 2015/7/14
N2 - An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.
AB - An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.
UR - http://www.scopus.com/inward/record.url?scp=84939811180&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.5b01798
DO - 10.1021/acs.orglett.5b01798
M3 - Article
SN - 1523-7060
VL - 17
SP - 3964
EP - 3967
JO - Organic Letters
JF - Organic Letters
IS - 16
ER -