Stepannikova, Kateryna O.; Vashchenko, Bohdan V.; Grygorenko, Oleksandr O.; Gorichko, Marian V.; Cherepakha, Artem Yu.; Moroz, Yurii S.; Volovenko, Yulian M.; Zhersh, Serhii published their research in European Journal of Organic Chemistry on December 21 ,2021. The article was titled 《Synthesis of Spirocyclic β- and γ-Sultams by One-Pot Reductive Cyclization of Cyanoalkylsulfonyl Fluorides》.Computed Properties of C9H13NO2 The article contains the following contents:
One-pot intramol. cyclization of novel sp3-enriched cyanoalkylsulfonyl fluorides into spirocyclic β- or γ-sultams is disclosed. The method relies on nitrile group reduction followed by sulfonylation of amino group thus formed upon mild conditions (NaBH4, NiCl2·6H2O in MeOH). Cyclization proceeds smoothly with considerable efficiency (48-84%, 10 examples) on up to 30 g scale. The cyanoalkylsulfonyl fluoride intermediates can be obtained via S-nucleophilic substitution in β-functionalized alkanenitriles or double alkylation of α-alkylthioacetonitrile, followed by oxidative chlorination with Cl2 and further reaction with KHF2. The title mono- and bifunctional sultams are advanced sp3-enriched building blocks for drug discovery and organic synthesis providing novel substitution patterns and frameworks mimicking saturated nitrogen heterocycles such as pyrrolidine/pyrrolidone. In the experiment, the researchers used Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5Computed Properties of C9H13NO2)
Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5) is a member of cyclopentanes. Although cyclopentane itself doesn’t have a single highly favoured conformation, a substituent on the cyclopentane ring can upset the balance of strains thereby favouring either the envelope or the half-chair.Computed Properties of C9H13NO2
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts