One‐pot three‐component synthesis of tetrasubstituted N—H pyrroles from secondary propargylic alcohols, 1,3‐dicarbonyl compounds and tert‐butyl carbamate

Abstract

Several tetrasubstituted NH pyrroles, functionalized with ester or ketone groups at C‐3 position, were prepared by one‐pot coupling of secondary propargylic alcohols with 1,3‐dicarbonyl compounds and tert‐butyl carbamate, via in situ deprotection of the corresponding pentasubstituted N‐Boc pyrroles. The three‐component coupling process was promoted by the combined use of the 16‐electron ruthenium(II) catalyst [Ru(η3‐2‐C3H4Me)(CO)(dppf)][SbF6] (dppf = 1,1′‐bis(diphenylphosphino)ferrocene) and trifluoroacetic acid (TFA). J. Heterocyclic Chem., (2010).

A Novel Approach for the Synthesis of 5‐Pyridylindolizine Derivatives via 2‐(2‐Pyridyl)pyridinium Ylides

“…Sequential transformations, multicomponent processes, and one‐pot procedures have become increasingly interesting because they offer simple and efficient synthetic ways to pyrroloazines .…”

ChemInform Abstract: A Novel Approach for the Synthesis of 5‐Pyridylindolizine Derivatives via 2‐(2‐Pyridyl)pyridinium Ylides.

“…Monosubstituted pyridinium N-ylides dipols are generally unstable compounds, and they are generated in situ by treatment of pyridinium salts with an organic or inorganic base. Sequential transformations, multicomponent processes, and one-pot procedures have become increasingly interesting because they offer simple and efficient synthetic ways to pyrroloazines [23][24][25][26][27][28][29][30].…”

Synthesis of densely functionalize pyrroles from unprotected carbohydrates

“…105 Later in 2010, the same group described a NH pyrrole synthesis method using the same Ru-complex jjby using the tert-butyl carbamate (Figure 1-45, II). 106 These two methods together made a versatile poly-substituted pyrrole synthesis strategy.…”