Active methylene compounds such as 5,5-dimethylcyclohexane-1,3-dione, cyclohexane-1,3-dione, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, 1,3-dimethyl-1H-pyrazol-5(4H)-one, and 3-methylisoxazol-5(4H)-one react with the 3-C position of N-confused porphyrin in THF for 5 min to afford a novel type of N-confused porphyrin derivatives in good yield without the need of any catalyst.

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The 1,3-dipolar cycloaddition reaction of 2-methyl-N-confused porphyrin with 2,6-dichlorobenzonitrile oxide yielded four isomeric monoadducts of carbachlorin type and one diadduct of carbabacteriochlorin type. Two major carbachlorin products, constituting 82% of the monoadducts, were shown to be structural precursors of the unique 2-aza-21-carbabacteriochlorin. Enantiomers of the most abundant isomer of 2-aza-21-carbachlorin (55% of all carbachlorin products) have been resolved. The crystal structures of 2-aza-21-carbabacteriochlorin and the most abundant isomer of 2-aza-21-carbachlorin were characterized by X-ray diffraction.

The 1,3‐dipolar cycloaddition of nitrile oxide to 2‐arylmethylidene‐2,3‐dihydro‐1H‐pyrrolizin‐1‐ones afforded new 4‐(aryl)‐3‐(2,6‐dichlorophenyl)‐1′H,4H‐spiro[isoxazole‐5,2′‐pyrrolizin]‐1′‐ones in moderate yields. The structures of all the products were characterized thoroughly by NMR, IR, MS, and elemental analysis together with X‐ray crystallographic analysis.

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