Ionic addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes

Recent Development of Regio‐ and Stereoselective Aminohalogenation Reaction of Alkenes

“…This ionic addition was further extended to the use of carbamate‐based nitrogen/halogen source, tert ‐butyl‐ N , N ‐dibromocarbamate (BBC) for aminobromination together with BF 3 · OEt 2 as reported by Zwierzak and Sliwinska35–36 Similar regioselectivity was observed with the final products being tert ‐Boc‐protected amines (Scheme ).…”

“…The contributing structures that are shown in Scheme (A, B and C) and the IR frequencies were consistent with the assigned structure. The interaction of the boron atom with the carbonyl group of BBC sufficiently ionizes the N–Br bond towards dissociation to form the Br + ion 36…”

Synthesis and Evaluation of 3‐[(2,4‐Dioxo‐1,3,8‐triazaspiro[4.6]undec‐3‐yl)methyl]benzonitrile Derivatives as Potential Anticonvulsants

“…The introduction of the substituent aryl groups at N-3 position of hydantoin ring was achieved via selective N-alkylation reaction by reacting aryl halide in presence of potassium carbonate and acetonitrile solvent [22,23]. Target key intermediate 7 was accomplished by deprotection of Boc group from compound 6 with dioxane in HCl and followed by basification with sodium carbonate solution [24]. The aim of the 7 was introduced to respective sulfonyl chlorides/acid chlorides at the Nposition of triazaspiro bicyclic moiety to lead to the desired compounds 8-37 for structure-activity relationship (SAR) study [25,26].…”

“…The results are presented in Table 2. The preliminary anticonvulsant screening showed that compounds 22,23,24,29,34, and 36 were inactive; however, many of these compounds were active against PTZ at 1.0 mmol/kg, among which compounds 11,18,31,and 32 presented 100% protection. Compounds 16,19, and 33 offered 66% protection.…”

“…Compounds 8,9,10,12,13,15,16,17,19,20,25,26,27,28,30,32,33, and 35 showed moderate protective effect in the MES and compounds 11, 18, and 31 were found to be 100% protective. Majority of the compounds, except 22,23,24,29,34, and 36, were active in MES tests making them useful for a broad spectrum of seizure types. The bioactivity in the MES test, exhibited by sulfonamide and amide derivatives such as 8-37, when the hydrogen group at the N-position was replaced by a phenyl ring, substitution of a small lipophilic group like fluoro group to the phenyl ring increases the anticonvulsant activity of 11, 18, 31, and 32.…”