Abstract:Indole-3,4- and 4,5-fused carbo- and heterocycles are ubiquitous in bioactive natural products and pharmaceuticals, and hence, a variety of synthetic approaches toward such compounds have been developed. Among these, cyclization and annulation of 3,5-unsubstituted, 4-substituted indoles involving an electrophilic aromatic substitution (SEAr) as the ring closure are particularly attractive, because they avoid the use of 3,4- or 4,5-difunctionalized indoles as starting materials. However, since 3,5-unsubstituted… Show more
“…The ring-opening of epoxides, whether in simple transformations or in cascade reactions, constitutes a powerful tool for the elaboration of a diverse class of acyclic and (poly)cyclic compounds—ranging from simple primary alcohols to complex natural products. 8 Nucleophilic aromatic substitution (S N Ar) is another hallmark reaction widely used for arene functionalization. 9 Notably, S N Ar is the second most frequently-used transformation after amide bond formation reaction in medicinal chemistry.…”
A one-pot, transition-metal-free, regioselective synthesis of spirooxindole derivatives containing benzimidazole-fused 1,4-benzoxazepine and benzosultam scaffolds has been developed.
“…The ring-opening of epoxides, whether in simple transformations or in cascade reactions, constitutes a powerful tool for the elaboration of a diverse class of acyclic and (poly)cyclic compounds—ranging from simple primary alcohols to complex natural products. 8 Nucleophilic aromatic substitution (S N Ar) is another hallmark reaction widely used for arene functionalization. 9 Notably, S N Ar is the second most frequently-used transformation after amide bond formation reaction in medicinal chemistry.…”
A one-pot, transition-metal-free, regioselective synthesis of spirooxindole derivatives containing benzimidazole-fused 1,4-benzoxazepine and benzosultam scaffolds has been developed.
“…Epoxide-opening cyclization represents another highly useful reaction that enables the construction of stereogenic sp 3 -carbon-bearing carbo- and heterocycles, often under full regio- and stereo-control. 4 In conjunction with our program directed toward the development of new cyclization strategies making use of intramolecular epoxide-opening reactions, 5 in 2020, we disclosed a base-mediated exo -selective epoxide-opening cyclization/intramolecular S N Ar cascade of ortho -fluorobenzenesulfonamide-tethered epoxides (Scheme 1A). 6 In the same year, Ma and co-workers synthesized 1-(arylamino)propan-2-ols via the reaction of EWG-substituted arylsulfonyl amides with terminal epoxides (Scheme 1B).…”
Reported herein is a transition-metal-free protocol for a regio- and diastereoselective synthesis of hydroxyalkyl-group embedded N-arylbenzo[b][1,4]oxazines and N-arylindolines based on an epoxide-opening cyclization/double Smiles rearrangement cascade of p-nosylamide-tethered epoxides. To...
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