Thiazepine

About: Thiazepine is a research topic. Over the lifetime, 327 publications have been published within this topic receiving 2591 citations. The topic is also known as: thiazepines.

Dibenzo-azepine, -diazepine, -Oxazepine und -thiazepine. 3. Mitteilung über siebengliedrige Heterocyclen†

Abstract: An examination of the BISCHLER-NAPIERALSKI reaction starting with 2-acylamino-diphenyl-amines, -sulfides, -methanes, and ethers, resp., is reported. Using phosphorous oxychloride or polyphosphoric acid, the products are azomethine derivatives of 5H-dibenzo[b, e]-1,4-diazepines, dibenzo[b, f]-l,4-thiazepines, llH-dibenzo[b, e]-azepines resp. dibenzo[b, f]-l, 4-oxazepines having the general formula III. The azomethine bridge in III can be hydrogenated catalytically or reduced with LiAlH4, to give derivatives of the general formula VI. Using several dialkylaminoalkyl chlorides in the presence of Na-amide, these derivatives are alkylated to VII. The basic strengths of several derivatives of III and VI are reported and the correlation between the basicity and the heteroatom in III and VI is discussed. The thiazepine derivatives show a noticeably lowered basicity, which we could not explain either by the inductive or by mesomeric effects of the sulfur bridge-atom.

An efficient assembly of heterobenzazepine ring systems utilizing an intramolecular palladium-catalyzed cycloamination.

Abstract: Azaheterocyclic compounds are interesting and medicinally relevant targets. Herein we disclose an improved synthesis into the oxazepine and thiazepine ring systems. The key step in the synthesis exploits recent advancements in the palladium-catalyzed amination reaction, which was utilized to form the seven-membered rings. General conditions for this reaction were Pd2dba3, P(t-Bu)3, NaO-t-Bu alone or with K2CO3, in toluene. The scope of the reaction was investigated, and has been shown to be effective on a variety of substrates as illustrated.

Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors: Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods

Abstract: The design and synthesis of a series of 6-methylidene penems containing [6,5]-fused bicycles (thiophene, imidazole, or pyrazle-fused system) as novel class A, B, and C beta-lactamase inhibitors is described. These penems proved to be potent inhibitors of the TEM-1 (class A) and AmpC (class C) beta-lactamases and less so against the class B metallo-beta-lactamase CcrA. Their in vitro and in vivo activities in combination with piperacillin are discussed. On the basis of the crystallographic structures of a serine-bound reaction intermediate of 2 with SHV-1 (class A) and GC1 (class C) enzymes, compounds 14a-l were designed and synthesized. Penems are proposed to form a seven-membered 1,4 thiazepine ring in both class A and C beta-lactamases. The interaction energy calculation for the enzyme-bound intermediates favor the formation of the C7 R enantiomer over the S enantiomer of the 1,4-thiazepine in both beta-lactamases, which is consistent with those obtained from the crystal structure of 2 with SHV-1 and GC1.

Process for the preparation of a thiazepine compound

Abstract: 11-(4-[2-(2-Hydroxyethoxy)ethyl]-piperazinyl)-dibenzo[b,f][1,4]thiazepine and the salts thereof possess antiandropaninergic activity, especially antipyschotic activity, and are prepared by reacting 11-piperazinyldibenzo[b,f][1,4]thiazepine with a compound of the formula:-(wherein X represent an atom or group removable as an anion and, where appropriate further reaction of the product obtained to yield the free base or salt as desired.