A facile route to 2-substituted N-Boc pyrrolidines

Synthesis of functionalised dithiocarbamates via N-(1-benzotriazolylalkyl)dithiocarbamates

“…31 However, we have located no reports of the introduction of functionalized N-substituents into either open-chain-or cyclic-dithiocarbamates. Our group has previously functionalized carbamates 18 (Scheme 4) via benzotriazolylalkylation [43][44][45] followed by nucleophilic displacement of benzotriazole with diverse nucleophiles, 46-54 such as organozinc reagents, 48,51 ester enolates, 54 or ammonia. 46,47,49 This approach also includes condensation of carbamates 18…”

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

“…Pyrrolidines monosubstituted at C-2 were easily generated from N-Boc-N-(benzotriazol-1-ylmethyl-3-chloropropylamine [49] 21 which in the presence of n-BuLi generated unstable anion 22 and then underwent intramolecular cyclization to form pyrrolidine 23 (Scheme 7) [50].…”

“…The benzotriazole moiety is readily substituted by Grignard reagents in the presence of zinc chloride to furnish 2-substituted pyrrolidines 24 (Scheme 8) [50].…”

1,2,3-Triazoles

“…The chemistry of compounds 668 is to some extent similar to that of the corresponding amines discussed above; however, increased stability of derivatives 668 and higher stability of the products of their reactions bring additional synthetic possibilities. Thus, the reaction with organozinc reagents, usually prepared in situ from zinc powder and alkyl bromides, leading to amides 664 is analogous to the reaction of the corresponding amines ( Scheme 104 ) 1998T7167 , 2000TL9691 . By contrast, the reaction with sodium alkoxides producing N -(α-alkoxyalkyl)amides 665 is unique to derivatives 668 1995JOC4002 , 2003JOC4338 .…”