This method had been employed for the addition of both azido
[52, 62, 63] and alkyne functionalities to the BODIPY core in reactions catalyzed by acetic acid and piperidine (Figure 29).
Arginine-rich TAT peptides (capable of penetrating plasma membrane directly) modified with clickable azido
group can be conjugated to oligonucleotides, cytotoxic drugs, or kinase inhibitors to facilitate cell penetration for therapeutic applications.
Whereas, the phenylarylazide substituent on the 2beta position of the tropane ring traversed into the external binding pocket interacting with the F319 residue on TM6 through [pi]-[pi] interactions supporting the recent cross-linking data demonstrating adduction of aryl azido
group to F320 in hDAT (F319 in rDAT).
These findings and the existance of wel known tautomerism between tetrazole and azido
forms in a lot of tetrazoles, are leading us to suggest the rapid equilibrium of each forms 4 and 5 with the azide form 3 as shown in Scheme 3 as a reasonable mechanism for explanation these observations.
Patai, Editor, The Chemistry of the Azido
Group Wiley, NewYork, (1971).
(9) Reverse transcriptase inhibitors (ex: 3' azido
3' deoxythymidine) (10) and natural products (ex.tclomestatin and sulfoquinovosyldiacyl glycerol) (11).
Initially, 2-chlorophenyl methanol 4 prepared from reduction of 4-chlorobenzaldehyde 3 was reacted with epichlorohydrin to give the aryl epoxide 5 [9,15] which was opened with sodium azide to afford azido
alcohol 6 in a 62% global yield from 4-chlorobenzaldehyde 3.
Anomalous heteroring opening of oxazinone by azide was supposed to occur via nucleophilic attack of azide either at C-2 of oxazinone ring followed by ring opening and addition of azido
group on cyano group to yield tetrazolylfuran derivative 10 or at C-4 of oxazinone followed by Curtius's rearrangement to isocyanate intermediate and then cyclization to give furo[3,2-d]imidazolone derivative 11 as summarized at Scheme 4.