N-tert-butoxycarbonyl-N-substituted hydrazines in SNAr displacements. Synthetic pathways to N-1-substituted anthrapyrazoles, aza-anthrapyrazoles and aza-benzothiopyranoindazoles

Autor:	Michael Ellis, L. Fiocchi, Ambrogio Oliva, A. Paul Krapcho, Ernesto Menta
Rok vydání:	2000
Předmět:	chemistry.chemical_compound Nucleophile Chemistry Nucleophilic aromatic substitution Yield (chemistry) Organic Chemistry Side chain Leaving group Trifluoroacetic acid Medicinal chemistry Anthrapyrazoles
Zdroj:	Journal of Heterocyclic Chemistry. 37:47-55
ISSN:	0022-152X
DOI:	10.1002/jhet.5570370108
Popis:	The synthesis of several N-tert-butoxycarbonyl(Boc)-protected-N-substituted hydrazines has been accomplished. The use of these protected hydrazines in SNAr substitutions leads to products in which the most nucleophilic nitrogen displaces the leaving group. Treatment of these compounds with trifluoroacetic acid readily removes the Boc-protecting group and the intermediates readily undergo cyclizations to yield N-1-substituted aza-benzothiopyranoindazoles, anthrapyrazoles and aza-anthrapyrazoles. Side chain buildup was employed in the synthesis of several aza-anthrapyrazoles.
Databáze:	OpenAIRE
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