5670-94-0Relevant articles and documents
The photochemistry of α-azidocinnamates - A reinvestigation
Meth-Cohn, Otto,Williams, Nicola J. R.,MacKinnon, Angus,Howard, Judith A. K.
, p. 9837 - 9848 (1998)
α-Azidocinnamates have been reported elsewhere to yield one diastereomer of a trimer in a stepwise and efficient manner by photolysis using quartz equipment. We find that use of pyrex filters or ketone sensitisation instead of quartz leads to high yields of the presumed intermediate diastereomeric pair of aziridinoimidazoline dimers, as does brief irradiation in quartz. These dimers have been characterised by spectral and crystallographic methods, and shown to oxidise with DDQ to give imidazoledicarboxylic esters, while the action of base on both dimer diastereomers leads to one rearranged dimer, a 1,2-dihydropyrimidine. Surprisingly, only a mixture of both diastereomeric dimers gives the trimer on further photolysis.
Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp3)-H and C(sp2)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds
Patel, Srilaxmi M.,P., Ermiya Prasad,Bakthadoss, Manickam,Sharada, Duddu S.
supporting information, p. 257 - 261 (2021/01/15)
Here we have demonstrated a visible-light-mediated metal-free organic-dye-catalyzed dehydrogenative N-insertion leading to highly substituted imidazoles and privileged dihydroisoquinoline-based imidazole derivatives via C(sp3)-H and C(sp2)-H bond functionalization. A sustainable, convenient, metal-free azidation/C-H aminative cyclization approach in the absence of stoichiometric oxidants is presented. This protocol involves a rare photoinduced iminyl radical as a key intermediate for the "N"insertion.
A direct cycloaminative approach to imidazole derivatives via dual C-H functionalization
Arepally, Sagar,Babu, Venkata Nagarjuna,Bakthadoss, Manickam,Sharada, Duddu S.
supporting information, p. 5014 - 5017 (2017/11/06)
Organoiodine(III)-promoted C(sp3)-H azidation was a key step for the cycloaminative process. An unprecedented method for metal-free dehydrogenative N-incorporation into C(sp3)-H and C(sp2)-H bonds for the synthesis of diverse imidazoles has been disclosed. The overall transformation involves the construction of four C-N bonds through hydroamination-azidation-cyclization sequence. The reaction can be easily handled and proceeds under mild conditions. Further, the potential of the present strategy is revealed by the practical synthesis of N-heterocyclic carbene (NHC) precursors.
