Bicyclische β‐Sultame: Darstellung aus monocyclischen β‐Aminothiolen und einige Eigenschaften

Abstract

2-Cyclaminmethanole 3 werden in 2-Cyclaminmethanthiole 7 umgewandelt, aus denen durch oxidative Chlorierung cyclisch substituierte Taurinsiiurechloride 8 zughglich sind. Durch Behandlung mit Basen werden 8 in die bicyclischen p-sdtame 9 ~pekmoskopisck Eigenschaften und solvolysevehalten von 9 werden diskutien Bicyclic p-Sultams: Synthesis from Monocyclic PAminothiols and Some PropertiesThe cyclamine methanethiols 7 are prepared from the corresponding akahols 3 and oxidatively transformed by treatment with chlorine into the cyclic substituted taurinechlorides 8. Upon treatment with bases, 8 is cyclized yielding the bicyclic p-sultams 9. Some spectroscopic properties and the solvolysis of 9 are briefly discussed.

Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine onto alkyl acrylates – Application towards the synthesis of 2-(methoxycarbonyl)indolizidine

“…8 Despite their inherent reactivity and synthetic potential, β-bromoamines 2a and 2b have only been studied to a limited extend up to now. 9 Subsequently, the conjugate addition of piperidines 2a,b onto alkyl acrylates was investigated.…”

“…Afterwards, the reaction mixture was poured into water (20 mL) and extracted with diethyl ether (3 × 15 mL). Drying (MgSO 4 ), filtration of the drying agent and removal of the solvent in vacuo afforded 2-(methoxycarbonyl)indolizidine (8) 3, 30.5, 30.8, 34.4, 34.7, 39.6, 51.7, 51.8, 52.7, 52.7, 56.7, 57.7, 63.6, 64.4, 175.6, 175.7 : C 65.54,H 9.35,N 7.64. Found: C 65.37,H 9.63,N 7.49.…”

Efficient Synthesis of Taurine and Structurally Diverse Substituted Taurines from Aziridines.

“…All solvents were used without purification. 1 H NMR spectra were recorded at 200 or 300 MHz in D 2 O and 13 C NMR spectra were recorded at 50 or 75.5 MHz in HCO 2 H with HCO 2 H as an internal standard at 166.3 ppm. IR spectra were determined in KBr.…”

Effect of Sulfur-Containing Side Chains on Transnitrosation of N-Nitroso Compounds of Thiazolidines

“…was added to a solution of the crude product in EtOH (20 mL) and the mixture was refluxed overnight. 28 Tetraethylenepentamine (1.85 mL, 1.2 eq.) was added dropwise to the mixture and refluxed for 3 h. After the mixture was cooled to room temperature, H2O (5 mL) was added, and the mixture was saturated with NaCl, and extracted with CH2Cl2 (10 mL × 4).…”