Barton–Zard synthesis

The Barton-Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanoacetate under basic conditions. It is named after Derek Barton and Samir Zard who first reported it in 1985.

The mechanism consists of five steps:

The nitro compound may be aromatic rather than just an alkene. The reaction has been used for the synthesis of polypyrroles, including porphyrins, as well as dipyrromethenes such as BODIPY.

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