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Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113
Graphical Abstract
Scheme 1: Thermal reaction of sydnones with symmetrical alkynes.
Scheme 2: Reaction of sydnones with strained cycloalkynes.
Scheme 3: Reaction of sydnones with didehydrobenzenes.
Scheme 4: Formation of isomeric pyrazole dicarboxylates.
Scheme 5: Mechanism of thermal cycloaddition between sydnones and alkynes.
Scheme 6: Mechanism of photochemical reaction of sydnones with symmetrical alkynes.
Scheme 7: HOMO–LUMO diagram for thermal [3 + 2]-cycloaddition of sydnones with alkynes.
Scheme 8: Synthetic strategy leading to 1,2-disubstituted pyrazoles.
Scheme 9: Unsuccessful reaction with phenylpropiolic acid.
Scheme 10: Synthetic strategy leading to 1,4,5-trisubstituted pyrazoles.
Scheme 11: Reaction of sydnones carrying in position 4- six-membered 2-N-heterocyclic ring.
Scheme 12: Strain-promoted sydnone alkyne cycloaddition (SPSAC).
Scheme 13: Synthesis of a key intermediate of niraparib.
Scheme 14: Reaction of sydnones with 1,3-/1,4-benzdiyne equivalents.
Scheme 15: Reaction of sydnones with heterocyclic strained cycloalkynes.
Scheme 16: Mono-copper catalyzed cycloaddition reaction.
Scheme 17: Di-copper catalyzed cycloaddition reaction.