Engaging the pyridine-DMAD zwitterion in a novel strategy for the selective synthesis of highly substituted benzene and cyclopentenedione derivatives.
[reaction: see text] The pyridine-mediated reaction of dimethyl acetylenedicarboxylate and cyclobutene-1,2-diones affords selective access to either hexasubstituted benzene derivatives or cyclopentenedione derivatives depending on the concentration of pyridine.
Nair
Vijay
V
Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum-695019, India. vijaynair_2001@yahoo.com
Pillai
Abhilash N
AN
Beneesh
P B
PB
Suresh
Eringathodi
E
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000480:Alkynes; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003503:Cyclobutanes / Q000737:chemistry*; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*
C110624:3-cyclobutene-1,2-dione; D000480:Alkynes; D001555:Benzene Derivatives; D003503:Cyclobutanes; D003517:Cyclopentanes; D011725:Pyridines; C022918:acetylenedicarboxylic acid dimethyl ester; D000114:Acetylene