Unexpected 20-membered macrocycles obtained by the condensation of α,α-dihalo-β-oxoaldehydes with diaminofurazan

Herein, we have isolated new 20-membered macrocycles by the simple condensation of α,α-dihalo-β-oxoaldehydes with diaminofurazan in acetonitrile. The interior and exterior sites of these macrocycles comprise hydrogen and halogen bond donor sites, respectively. Depending on the electron donating or a...

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Bibliographic Details
Published inNew journal of chemistry Vol. 48; no. 29; pp. 12869 - 12872
Main Authors Guseinov, Firudin I, Ovsyannikov, Viacheslav O, Shuvalova, Elena V, Kustov, Leonid M, Kobrakov, Konstantin I, Samigullina, Aida I, Mahmudov, Kamran T
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 22.07.2024
Royal Society of Chemistry
Subjects
Acetonitrile
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
1,2,5-OXADIAZOLE
MECHANISMS
OXYHALOGENATION
ALKYNES
FURAZANS
DERIVATIVES
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Summary:Herein, we have isolated new 20-membered macrocycles by the simple condensation of α,α-dihalo-β-oxoaldehydes with diaminofurazan in acetonitrile. The interior and exterior sites of these macrocycles comprise hydrogen and halogen bond donor sites, respectively. Depending on the electron donating or accepting character of the substituents at the exterior sites of macrocyclic scaffolds, the average cavity diameters range from 8.15 to 8.47 Å. Reaction of α,α-dihalo-β-oxoaldehydes with diaminofurazan in acetonitrile affords unexpected 20-membered macrocycles.
Bibliography:For ESI and crystallographic data in CIF or other electronic format see DOI
Electronic supplementary information (ESI) available: Experimental procedures, analytical data and spectra. CCDC
https://doi.org/10.1039/d4nj01789g
2338045-2338047
ISSN:1144-0546
1369-9261
DOI:10.1039/d4nj01789g