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Spiro Compounds Having a Nonplanar 1,4‐Dihydropyridine Ring from Diaziridinimines and Dimethyl Acetylenedicarboxylate
Author(s) -
Quast Helmut,
Ross KarlHeinz,
Spiegel Erwin,
Peters Karl,
von Schnering Hans Georg
Publication year - 1977
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197701771
Subject(s) - dimethyl acetylenedicarboxylate , cycloaddition , ring (chemistry) , adduct , reagent , chemistry , dihydropyridine , medicinal chemistry , organic chemistry , catalysis , calcium
The unpredictable reagent dimethyl acetylenedicarboxylate (1) reacts with the diaziridinimine (2) to give a 3:1 adduct shown by X‐ray structure analysis to have the spiro structure (3) . The unexpected formation of (3) is explained by two cycloadditions, ring opening, and another cycloaddition.