RESUMO
The development of a microwave-assisted, intermolecular S(N)Ar protocol for the synthesis of a 126-member benzothiaoxazepine-1,1-dioxide library is reported. Diversification of 12 benzothiaoxazepine-1,1-dioxides was achieved in rapid fashion utilizing a variety of 2° amines and amino alcohols to generate an 80-member library. A second 48-member library was subsequently generated via a two-step alkylation, intermolecular S(N)Ar diversification protocol.
Assuntos
Benzotiadiazinas/síntese química , Técnicas de Química Combinatória/métodos , Micro-Ondas , Oxazepinas/síntese química , Óxidos/síntese química , Alquilação , Amino Álcoois/química , Benzotiadiazinas/química , Modelos Químicos , Oxazepinas/química , Óxidos/química , Sulfonamidas/químicaRESUMO
A monomer-on-monomer (MoM) Mitsunobu reaction utilizing norbornenyl-tagged (Nb-tagged) reagents is reported, whereby purification was rapidly achieved by employing ring-opening metathesis polymerization, which was initiated by any of three methods utilizing Grubbs catalyst: (i) free catalyst in solution, (ii) surface-initiated catalyst-armed silica, or (iii) surface-initiated catalyst-armed Co/C magnetic nanoparticles.
Assuntos
Polímeros/síntese química , Magnetismo , Nanopartículas Metálicas/químicaAssuntos
Compostos Heterocíclicos/química , Compostos Heterocíclicos/síntese química , Hidrocarbonetos Bromados/química , Hidrocarbonetos Bromados/síntese química , Hidrocarbonetos Fluorados/química , Hidrocarbonetos Fluorados/síntese química , Oxazepinas/química , Compostos de Sulfidrila/química , Química Orgânica , Ciclização , Micro-Ondas , Estrutura MolecularRESUMO
A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.
