An efficient synthesis of pyrrolo2,3-dpyrimidines via inverse electron demand diels-alder reactions of 2-amino-4-cyanopyrroles with 1,3,5-triazines

The scope of the inverse electron demand Diels-Alder reaction of 2-amino-4-cyanopyrroles (3a-e) with 1,3,5-triazines (1, 2) is reported. This methodology is suitable for one-pot syntheses of highly substituted and highly functionalized pyrrolo[2,3-d]pyrimidines that are the central heterocyclic nucl...

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Published inJournal of organic chemistry Vol. 67; no. 24; p. 8703
Main Authors Dang, Qun, Gomez-Galeno, Jorge E
Format Journal Article
LanguageEnglish
Published 29.11.2002
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ISSN0022-3263
DOI10.1021/jo026309d

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Summary:The scope of the inverse electron demand Diels-Alder reaction of 2-amino-4-cyanopyrroles (3a-e) with 1,3,5-triazines (1, 2) is reported. This methodology is suitable for one-pot syntheses of highly substituted and highly functionalized pyrrolo[2,3-d]pyrimidines that are the central heterocyclic nucleus of various nucleoside natural products such as toyocamycin, sangivamycin, and tubercidin.The scope of the inverse electron demand Diels-Alder reaction of 2-amino-4-cyanopyrroles (3a-e) with 1,3,5-triazines (1, 2) is reported. This methodology is suitable for one-pot syntheses of highly substituted and highly functionalized pyrrolo[2,3-d]pyrimidines that are the central heterocyclic nucleus of various nucleoside natural products such as toyocamycin, sangivamycin, and tubercidin.
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ISSN:0022-3263
DOI:10.1021/jo026309d