Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinones

Abstract

We describe the efficient synthesis of 4,7,8,10-tetrasubstituted-(((4S,10aS)-3-oxo-3,4,10,10a-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)alkyl)amides on solid phase via tandem N-acyliminium ion cyclization-nucleophilic addition reactions. The synthesis proceeded with complete stereocontrol of a newly formed stereogenic center, provided crude material of high purity, and used commercially available building blocks under mild reaction conditions.

Polymer‐Supported Stereoselective Synthesis of (1S,5S)‐6‐Oxa‐3,8‐diazabicyclo[3.2.1]octanes

“…Commercially available Rink resin (100–200 mesh, 0.66 mmol/g) and Wang resin (100–200 mesh, 1.0 mmol/g) were used. Individual synthetic steps for the synthesis of resins 1 – 4 have been described in our recent publications 5,46. CCDC‐932765 [for 6(1,1,6) ] contains the supplementary crystallographic data for this paper.…”

“…The existing compound collections typically display a low frequency of sp 3 ‐hybridized carbons and chiral centers when compared with drugs and natural products 4. To fill the gap in chemical space, our ongoing research is focused on the design and synthesis of compound collections that are characterized by nature‐inspired, nonplanar structures (i.e., those that include sp 3 carbons) and the formation of stereogenic centers with stereocontrol 5–7…”

From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone

“…The reaction conditions for the individual steps of the synthesis have been reported in previous communications. 27,28 Analytical Data of Individual Compounds. (2S,6R)-3-((4-Nitrophenyl)sulfonyl)-2,3,4,5,6,7-hexahydro-1H-6,2-(epiminomethano) azocino [5,4-b]indol-13-one [(S,R)-5f].…”

One‐pot synthesis of benzimidazole‐pyrazines and their anticancer activities

“…Compound II was constructed via a Ugi/deprotection/cyclization (UDC) strategy, followed by a nucleophilic substitution reaction in good yields ; this compound was also reported to be obtained via an intramolecular Goldberg reaction in one step using CuI as a catalyst . On the other hand, compound III was synthesized by an efficient solid‐phase reaction via N ‐acyliminium ion cyclization‐nucleophilic addition under mild reaction conditions using commercially available starting materials . Compound IV was synthesized by Jordan et al as a GABA‐A receptor through five steps .…”