Study on the chemical reactivity of a cyano group in the 5-position of 4 and/or 6-substituted pyrrolopyrimidine nucleosides

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Title Study on the chemical reactivity of a cyano group in the 5-position of 4 and/or 6-substituted pyrrolopyrimidine nucleosides
Publication Type dissertation
School or College College of Pharmacy
Department Medicinal Chemistry
Author Schram, Karl Howard
Date 1973-06
Description The reactivity of the cyano group at the 5-position of the pyrrolopyrimidine nucleosides has been studied with various groups in the 4- and/or 6-positions. The susceptibility of the cyano group toward nucleophilic substitution under basic conditions as influenced by amino groups was found to be in the order: no amino group at positions 4 or 6>4-amino>6-amino>4,6-diamino. The decreased reactivity of the amino substituted derivatives is due to electron release by the amino groups. During the investigation of the reaction of 4-chloro-5-cyano-7-(B-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine with methyl hydrazine, a new tricyclic nucleoside, 6-amino-4-methyl-8-(B-D-ribofuranosyl)(4H ,8H)-pyrrolo[4,3,2-de]pyrimido[4,5-c]pyridazine, was synthesized. Subsequent studies showed that the intermediate was 5-cyano-4-N-l-methylhydrazino-7-(3-D-riboguranosyl)pyrrolo[2,3-d]pyrimidine and cyclized in situ to the tricyclic derivative.
Type Text
Publisher University of Utah
Subject Biochemistry; Antileukemic Agents
Subject MESH Nucleosides; Pyrroles
Dissertation Institution University of Utah
Dissertation Name PhD
Language eng
Relation is Version of Digital reproduction of "A study on the chemical reactivity of a cyano group in the 5-position of 4 and/or 6-substituted pyrrolopyrimidine nucleosides". Spencer S. Eccles Health Sciences Library. Print version of "A study on the chemical reactivity of a cyano group in the 5-position of 4 and/or 6-substituted pyrrolopyrimidine nucleosides". available at J. Willard Marriott Library Special Collection. QP6.5 1973 .S33.
Rights Management © Karl Howard Schram.
Format application/pdf
Format Medium application/pdf
Format Extent 1,712,695 bytes
Identifier undthes,4570
Source Original: University of Utah Spencer S. Eccles Health Sciences Library (no longer available).
Funding/Fellowship National Defense Education Act, Title IV Fellowship
Master File Extent 1,712,717 bytes
ARK ark:/87278/s6930w3f
Setname ir_etd
ID 191874
Reference URL https://collections.lib.utah.edu/ark:/87278/s6930w3f
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