Synthetical pharmaceutics. 9‐ and 10‐Oxo derivatives of 9,10‐dihydro‐4H‐benzo‐[4,5]‐cyclohepta[1,2b]thiophenes

Abstract

Synthetical pharmaceutics. 9-and 10-0x0 derivatives of 9,10-dihydro-4H-benzo-[4,5]-cyclohepta[l,2-b]thiophenes. -Zusammenfassung. Vcrschiedene Synthesen zur Herstellung von ~-~xo-9,10-dihydro-4H-benzo[4,5]cyclohcpta[l, 2-blthiophenen 17 und lO-Ox0-9,lOdihydro-4H-benzo[4,5]cyclohepta[l,2-b]thiophenen 18 (25), mit dcr l-.llkyl-4-piperidyliden-Gruppe in 4-Stcllung, ausgchend van 9,10-Dihydro-4 H-benzo[4,5]cyclohepta[l, 2-blthiophen-4m e n 1 bzw. Folgestufen davon, werden beschrieben. Als weitcrc Derivatc sind die N-Oxide 26, die 9-und 1O-I-Iydroxv-I)erivate 27 und 28, die 9und 10-Oximc 29 untl 30 sowie ein 9,lO-Diketon 31 hergestellt wordcn. 1. Einleitung. -In Weiterfuhrung der Arbeiten auf dern Gebiet des 9,lO-Dihydro-4H-benzo[4,5]cyclohepta[l, 2-b]tliiophen-Tricpclus [I] wurden die 9und 10-0x0-Derivnte mit der 1-Alkyl-4-piperidyliden-Gruppe in 4-Stellung hergestellt (A und B).

Acrylamide derivatives as antiallergic agents. 2. Synthesis and structure activity relationships of N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3-(3-pyridyl)acrylamides

“…Ring deactivating groups, such as cyano (24) and nitro (33), suppress activity, whereas the effect of ring activation is less clear. While the p-amino (27), p-dimethylamino (28), and 3-bromo-p-(dimethylamino)be.nzyl (31) piperazine compounds exhibit blood pressure lowering 0022-2623/89/1832-0593$01.50/0 © 1989 American Chemical Society…”

(Benzo[4, 5]cyclohepta[l, 2‐b]thiophen‐4‐ylidene)acetic Acids: Novel Non‐ulcerogenic Antiinflammatory Agents

“…The synthesis of a number of functionalized benzo [4,5]cyclohepta[ 1,241thiophene derivatives starting from 9a [13] was well known from previous work in our laboratories [14]. The acrylic-acid functionality in 7 was introduced by a Horner reaction on the methoxy ketone 10a [14].…”

“…The acrylic-acid functionality in 7 was introduced by a Horner reaction on the methoxy ketone 10a [14]. Subsequent basic hydrolysis of the ester group followed by acidic hydrolysis of the enol-ether group led to the desired product 7.…”

“…FC (toluene) gave 0.7 g (33%) of9a as a dark oil. 9,IO-Dibromo-9,IO-dihydro-4H-benzo(4,S]cyclohepta[l,2-b]thiophen-4-one (14a) was synthesized as described [14]. Using the same procedure, 14-were prepared.…”

“…The conversion of ketones 9a-g to the desired 10-methoxy-substituted ketones 1Oa-g was achieved following the described procedure (bromination followed by treatment with MeOH and KOH) [14], and reaction of ketones 10a-g with alkyl (dialkoxyphosphory1)acetates (Horner-Emmons reaction) gave the (E/Z)-mixtures 15a-g. The isomers were separated by column chromatography (silica gel) and subsequently hydrolyzed to the corresponding (heteroary1idene)acetic acids 8a-g.…”