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Synthesis of 4-substituted 2-aminopyrrolo[2,3-d]pyrimidine 2′,3′-dideoxyribonucleosides

✍ Scribed by Seela, Frank ;Muth, Heinz-Peter


Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
578 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis


Abstract

A number of new 2‐aminopyrrolo[2,3‐d]pyrimidine N‐7‐(2′,3′‐dideoxyribonucleosides) (11–13 and 15) were synthesized. These are related to 7‐deaza‐2′,3′‐dideoxyguanosine (14), but carry various substituents at C‐4. 2‐Amino‐4‐chloro‐7‐(2′,3′‐dideoxy‐β‐D‐glycero‐pentofuranosyl)‐7__H__‐pyrrolo[2,3‐d]‐pyrimidine (3) was used as a common intermediate, and was obtained from the corresponding 2′‐deoxyribonucleoside 4 by selective silylation of 5′‐OH and Barton deoxygenation of 3′‐OH.


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✍ Pavlo E. Shynkarenko; Sergiy V. Vlasov; Sergiy M. Kovalenko; Svitlana V. Shishki 📂 Article 📅 2010 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 185 KB 👁 1 views

## Abstract magnified image The interaction of both 2‐iminocoumarin‐3‐carbonitriles and 2‐iminocoumarin‐3‐carbothioamides with 2‐aminothiophen‐3‐carboxamides lead to formation of 3‐(4‐oxo‐3,4‐dihydrothieno[2,3‐__d__]pyrimidin‐2‐yl)‐2‐iminocoumarins in two steps. The simplicity of the procedure, as