C–H Phosphonation of Pyrrolopyrimidines: Synthesis of Substituted 7- and 9‑Deazapurine-8-phosphonate Derivatives

The Mn­(OAc)₃-promoted C–H phosphonation of 7-deazapurines (pyrrolo­[2,3-<i>d</i>]­pyrimidines) and 9-deazapurines (pyrrolo­[3,2-<i>d</i>]­pyrimidines) with diethylphosphite was developed. The reactions occur regioselectively at position 8 both in 7 and 9-deazapurines, leading to new deazapurine-8-phosphonate derivatives, which can be further modified and transformed to 6-(het)­aryl-deazapurine derivatives or deprotected to free phosphonic acids

C–H Imidation of 7‑Deazapurines

We developed and presented here a ferrocene-catalyzed C–H imidation of 7-deazapurines (pyrrolo­[2,3-<i>d</i>]­pyrimidines) with <i>N</i>-imidyl peroxyesters. The reactions occur regioselectively at position 8 in 7-deazapurines, leading to a series of 8-succinimido-, phtalimido-, or naphthalimido-7-deazapurine derivatives. Attempted hydrazinolysis of resulting 8-imidyl-7-deazapurines led to corresponding 8-amino-7-deazapurine, which was very unstable and quickly decomposed

C–H Imidation of 7‑Deazapurines

We developed and presented here a ferrocene-catalyzed C–H imidation of 7-deazapurines (pyrrolo­[2,3-<i>d</i>]­pyrimidines) with <i>N</i>-imidyl peroxyesters. The reactions occur regioselectively at position 8 in 7-deazapurines, leading to a series of 8-succinimido-, phtalimido-, or naphthalimido-7-deazapurine derivatives. Attempted hydrazinolysis of resulting 8-imidyl-7-deazapurines led to corresponding 8-amino-7-deazapurine, which was very unstable and quickly decomposed