One-pot regio- and chemo-selective synthesis of thiaazatricyclododecane

Stereoselective synthesis of fused-, spiro- and bridged heterocycles via cyclization of isoquinolinium salts: a recent update

“…Alizadeh and co-workers devised a highly regio-and chemoselective method to synthesize polysubstituted thiaazatricyclododecanes by a sequential four-component reaction. 64 They synthesized thiaazatricyclododecanes 161 via the reaction of methyl-4-chloro-3-oxobutanoate 160 with betaine 162 generated in situ from the reaction of isoquinoline 11, 2-bromoacetophenones 2 and isothiocyanates 159 (Scheme 45). The formation of a single stereoisomer was confirmed by NMR, mass and X-ray crystallographic studies.…”

Cyclative MCRs of Azines and Azinium Salts

“…Later on a novel and highly regio‐ and chemo‐selective heteroannulation method for the synthesis of polysubstituted thiaazatricyclododecanes ( 316 ) by a tandem four‐component reaction of isoquinoline ( 312 ), bromoacetophenones ( 313 ), aryl isothiocyanates ( 314 ), and methyl 4‐chloro‐3‐oxobutanoate ( 315 ) has been reported by the same group. [ 175 ] The reaction is suitable for various bonds including C–N, C–S, and C–C at mild reaction conditions (Scheme 62). The reaction of isoquinoline ( 312 ) with 2‐bromoacetophenone ( 313 ), phenyl isothiocyanate ( 314 ) and methyl 4‐chloro‐3‐oxobutanoate ( 315 ) in the presence of triethylamine gives intermediate ( 317 ).…”

“…[120,121] The catalytic multicomponent [ The same group developed later on a one-pot, straight forward domino [5 + 2]/[2 + 2] cycloaddition reactions leading to pentacyclic heterocycles. [122] Pyridinium zwitterions (174) acted as specific 1,5-dipole in metal-free [5 + 2] dipolar cycloadditions reaction with (175). It resulted in the formation of 1,4-benzodiazepines whose further [2 + 2] cycloadditions with other arynes lead to the end product (176) (Scheme 34).…”

Crystal structure of (diethyl ether-κO)[5,10,15,20-tetrakis(2-isothiocyanatophenyl)porphyrinato-κ4 N]zinc diethyl ether solvate

“…Isothiocyanates serve as versatile starting materials for a variety of functional groups (Batey & Powell, 2000;Ding et al, 2011;Serra et al, 2014;Guo et al, 2010;Shin et al, 2000;Kosurkar et al, 2014;Alizadeh et al, 2016;Rao et al, 2015). Included in porphyrin scaffolds, isothiocyanates may serve as precursors for the synthesis of tetratopic ligands with fourfold symmetry.…”