Novel Pyrrolo[2,3-d]pyrimidine Ring forming Methodology |
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| Authors: | Samuel E Watson Farrah Khandkar My Bui Anatoly Markovich Edward C. Taylor |
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| Affiliation: | 1. Department of Chemistry , Long Island University, One University Plaza , Brooklyn, N.Y., 11201;2. Department of Chemistry , Princeton University , Princeton, N.J., 08544 |
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| Abstract: | A short, succinct route to biologically active and medicinally important pyrrolo[2,3-d]pyrimidines has been developed starting from readily available acyclic aldehydes. A very efficienttwo step sequence involving a Knoevenagel condensation followed by copper mediated 1,4-conjugate of vinyl magnesium bromide sets up the acyclic precursor. Then, guanidine cyclization followed by a palliduim catalyzed amination reaction or ozonolytic cleavage of the vinyl substituent followed by guanidine cyclization and intramolecular imine formation complete the synthesis. |
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