Alkylations of 1-(4-chlorophenyl)-3-ethoxy-1H-isoindole

Abstract

ion of the benzylic proton from l-(4-chlorophenyl)-3-ethoxy-l/f-isoindole (la) with sodium hydride gave the corresponding carbanion which was alkylated with a variety of alkyl halides to give the imino esters ld-i, 5 while oxidation yielded lb. Hydrolysis led to the lactams 2d-i, 6 and 2-(4-chlorobenzoyl)benzoic acid ethyl ester, respectively. The tetrazolo compounds 4e-l were prepared via the intermediates 3e-i. Heating of 6 resulted in the formation of 7a which could be reduced to the amine 7b. From the imino ester 5 the triazole 9 was prepared.Recently we have described the preparation of l-(4-chlorophenyl)-3-ethoxy-l/í-isoindole (la) and its conversion to l-amino-4-(4-chlorophenyl)phthalazine1 via reaction with hydrazine. As a continuation of our efforts to explore the synthetic usefulness of la we have prepared2 a variety of 3alkylated derivatives and converted them to the novel tricyclic systems.

Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

“…Alkylation of the sodium salt of the ethoxyisoindoline 27 with bromomethyl methyl ether gave 28b. Heating the known 28a 22 and 28b with 3-aminopropanol gave 3-hydroxypropylamines 29a and 29b. When these were treated with the I 2 /(C 6 H 5 ) 3 P complex in the presence of imidazole, the resultant 3-iodopropylamino intermediates cyclized to 6-alkyl-homomazindols 30 and 31 (Scheme 3).…”

Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 2. Isoindoloquinolines, isoindoloisoquinolines. (Review)

“…Compound 138 exhibits coccidiostatic activity [59] (coccidia are intracellular parasites giving rise to coccidiosis -an invasive disease of humans and animals -and mainly parasitize the epithelium of the digestive system). Lactim ethers can be used for the synthesis of isoindolo[2,1-b]isoquinolines [61,62]. Thus, the reaction of the carbanion generated from 1-(p-chlorophenyl)-3-ethoxy-1H-isoindole (139) with o-bromomethylbenzoic ester leads to the benzyl derivative 140, the acid hydrolysis and pyrolysis of which give isoindolo[2,1-b]-isoquinoline 142.…”

“…Thus, the reaction of the carbanion generated from 1-(p-chlorophenyl)-3-ethoxy-1H-isoindole (139) with o-bromomethylbenzoic ester leads to the benzyl derivative 140, the acid hydrolysis and pyrolysis of which give isoindolo[2,1-b]-isoquinoline 142. Treatment of the iminoester 140 with hydrazine leads to a sequence of transformations, ending up in the formation of the triazole 143 [61]. The Stevens rearrangement of quaternary spiroindane salts 147 with sodium hydride, phenyllithium, or sodium hydroxide leads to the formation of the isoindoloisoquinolines 148 with low yields [63].…”

Σύνθεση Και Μελέτη Δομής Συμπυκνωμένων Βενζοδιαζεπινικών Παραγώγων Με Πιθανή Βιολογική Δράση

“…Στη βιβλιογραφία αναφέρονται πολλά παραδείγματα 1,5-βενζοδιαζεπινών με βιολογική δράση, οι οποίες έχουν έναν ή δύο ετεροκυκλικούς δακτυλίους σε διαφορετική θέση του επταμελούς δακτυλίου. Είναι γνωστά παραδείγματα αζιρινο-, [77][78][79] πυρρολο-, [80][81][82][83] φουρο-, [84][85][86] βενζοφουρο-, 87 θειενο-, [88][89] πυραζολο-, [90][91][92][93] ιμιδαζολο-, θειαζολο-, [94][95] ισοθειαζολο-, τριαζολο-, [96][97][98][99][100] οξαδιαζολο-, [101][102] πυριδο-, [103][104][105][106][107] κινο, 108 πυρανo-, βενζοπυρανο-, πυριμιδο-, [116][117][118] πυραζινο-, [119][120] κινοξαλινο- [112][113][114][115][116][117][118][119][120]…”