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A reaction between cynichrodenoic acid, (eta5-C5H4COOH)Cr(CO)2NO (6) and phosphorus pentachloride produces cynichrodenoyl chloride (11) in high yield.Subsequent reaction of 11 with sodium azide affords cynichrodenoyl azide (12), which undergoes Curtius rearrangement to form cynichrodenyl isocyanate (13).Subsequent hydrolysis of isocyanate 13 in aqueous KOH solution yields aminocynichrodene (14).Azide 12 also undergoes Curtius rearrangement in the presence of benzyl alcohol to produce benzyl N-cynichrodenylcarbamate (15).Reactions of acid chloride 11 with ammonia, dimethylamine or aniline lead to the corresponding carboxamides (16-18).Amide 16 is readily dehydrated to produce cynichrodenecarbonitrile (19).Reactions of acid chloride 11 with either benzyl alcohol or hydroxymethylferrocene generate the corresponding esters (20-21), whereas treatment of a tetrahydrofuran solution of 11 with pyridine affords cynichrodenecarboxylic anhydride (22) in low yield.Reactions of acetylcynichrodene (2) with organolithium reagents, leading to both carbonyl addtion and condensation products, have been investigated.Treatment of 2 with lithium diisopropylamide in diethyl ether solution produces the self-condensation product 1,3-dicynichrodenyl-but-2-en-1-one (24).Acetyl derivative 2 and benzaldehyde also undergo Claisen-Schmidt condensation in the presence of lithium diisopropylamide to afford cinnamoylcynichrodene (27).

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion