Adamantylation of azoles by 1,3-dehydroadamantane: I. N-adamantylation of imidazoles by 1,3-dehydroadamantane

(Z)-2′-((Adamantan-1-yl)thio)-1,1′-dimethyl-2′,3′-dihydro-[2,4′-biimidazolylidene]-4,5,5′(1H,1′H,3H)-trione

“…The analysis (see supplementary) showed that the by-product was (Z)-2 -((adamantan-1-yl)thio)-1,1 -dimethyl-2 ,3 -dihydro-[2,4 -biimidazolylidene]-4,5,5 (1H,1 H,3H)-trione (5, Scheme 2, Figure 2). as ordinary N-H bonds [25][26][27][28]. In this regard, we carried out the modification of 2-thiohydantoin and its 3-alkyl-and aryl-derivatives using 1,3-DHA.…”

“…Molbank 2023, 2023, x FOR PEER REVIEW 2 of as ordinary N-H bonds [25][26][27][28]. In this regard, we carried out the modification of 2-thio hydantoin and its 3-alkyl-and aryl-derivatives using 1,3-DHA.…”

“…3,7 .0. 1,3 ]decane, 1,3-DHA, 2, Scheme 1) is a convenient reagent for the direct introduction of the adamantyl moiety into the molecules of various organic compounds with activated C-H [24] as well as ordinary N-H bonds [25][26][27][28]. In this regard, we carried out the modification of 2thiohydantoin and its 3-alkyl-and aryl-derivatives using 1,3-DHA.…”

Adamantylation of azoles with 1,3-dehydroadamantane. Selective N-adamantylation of pyrazoles

“…We previously synthesized a series of N-adamantylsubstituted imidazoles by reaction of 1,3-dehydroadamantane with the corresponding imidazoles [8]. In the present communication we report for the first time on the N-adamantylation of pyrazole (IIa), 4-bromopyrazole (IIb), and 3,5-dimethylpyrazole (IIc) with 1,3-dehydroadamantane (I).…”

“…However, this method ensures fairly poor yields of the target products and requires strongly acidic medium. A promising method for the preparation of N-adamantylsubstituted pyrazoles involves as initial compound strained [3.3.1]propellane, 1,3-dehydroadamantane (I), which is characterized by a high proton affinity (pyrazoles are weak NH acids; pK a of unsubstituted pyrazole is 14.0 [7])We previously synthesized a series of N-adamantylsubstituted imidazoles by reaction of 1,3-dehydroadamantane with the corresponding imidazoles [8]. In the present communication we report for the first time on the N-adamantylation of pyrazole (IIa), 4-bromopyrazole (IIb), and 3,5-dimethylpyrazole (IIc) with 1,3-dehydroadamantane (I).…”