1999
DOI: 10.1016/s0040-4020(99)00162-3
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Hydroformylation of 1,4-diolefins in the presence of primary amines leading to heterocyclic compounds

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Cited by 34 publications
(24 citation statements)
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“…Their formation can be rationalized in terms of a mechanism akin to that delineated for the synthesis of pyrroles starting from 1,4-pentadienes under hydroformylation conditions. [14] The 1,5-diazacyclooctanes 6a and 6b both result from an iso,iso-hydroformylation process. A nine-membered ring product, as might be expected [13] to result from an n,isohydroformylation, is not observed.…”
Section: Resultsmentioning
confidence: 99%
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“…Their formation can be rationalized in terms of a mechanism akin to that delineated for the synthesis of pyrroles starting from 1,4-pentadienes under hydroformylation conditions. [14] The 1,5-diazacyclooctanes 6a and 6b both result from an iso,iso-hydroformylation process. A nine-membered ring product, as might be expected [13] to result from an n,isohydroformylation, is not observed.…”
Section: Resultsmentioning
confidence: 99%
“…1,25.8,28.8,29.4 (CH,8),31.5,31.8,32.5 (CH 2 ,7), 50. 4, 50.8, 51.0, 51.3, 51.3, 51.5, 51.5 (2 ϫ CH 2 , 4 ϩ 6), 46.3, 49.0, 51.7, 54.1 (CH 2 ,9),58.5,58.6,59.0,59.2 (CH 2 ,15),126.6,126.7,126.7 (CH,19), 127.9, 128.0, 128.0 (CH,17/18),128.8,128.9,129.1 (CH,18/17),139.6,139.7,139.9,140 (11), 65 (16), 41 (14). Ϫ C 29 H 43 N 3 O (449.7): calcd.…”
Section: Reaction Of N-acetyldiallylamine (1a) With 2-propylamine (4bmentioning
confidence: 99%
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“…[6] Tr ansition metal-catalyzed cyclization/ring expansion of functionalized alkynes, [7] hydroformylation of 1,4-dienes followed by condensation with primary amines, [8] and other reactions [9] have also been applied for the synthesis of cyclopenta[b]pyrrole derivatives.…”
mentioning
confidence: 99%
“…To our delight, a1 :1 molar ratio reactiono ccurred in the presence of 50 mol% p-TsOH·H 2 Oa st he promoter in dichloromethane at ambient temperature,f orming the target product 3a in 32% yield with excellent diastereoselectivity (dr > 20:1) ( Among the tested solvents (dichloromethane,1 ,2-dichloroethane,a cetonitrile, toluene andT HF), bothd ichloromethane and1 ,2-dichloroethane were found to provide suitabler eactionm edia, in contrast, the reaction hardly proceeded in THF (Table 1, entries 5a nd [8][9][10][11]. Elevating the reactiont emperature to 40-60 8 8C loweredt he formation of 3a (Table 1, entries 12 and 13).…”
mentioning
confidence: 99%