Über Verbindungen mit Urotropin‐Struktur, L. Cyclisierungsreaktionen ausgehend von cis‐3.5‐Diamino‐cyclohexanol

Abstract

Ausgehend vom 3.5-Dinitro-phenol (1) wird eine neue, ergiebige Methode zur Herstellung des cis-3.5-Diamino-cyclohexanols, gewonnen als Diacetylderivat (3, beschrieben. Durch Kondensation von 5 und von cis-3.5-Bis-benzolsulfonylamino-cyclohexanol (8) rnit Orthoameisensaure-triathylester sind N.N'-Diacetyl-(4) und N.N'-Bis-benzolsulfonyl-2-oxa-4.lOdiaza-adamantan (6) zug8nglich. Gleichzeitig wurde durch intramolekulare Umacetalisierung das 3-Methyl-4-acetyl-2-oxa-4.IO-diaza-adamantan (3) erhalten. Compounds with Urotropin Structure, L '1Cyclization Reactions Starting with cis-3.5-Diaminocyclohexanol cis-3.5-Diaminocyclohexanol, isolated as the diacetyl derivative (3, is prepared in good yields by a new method starting from 3.5-dinitrophenol (I). Condensation of 5 and cis-3.5bis(phenylsulfonylamino)cyclohexanol (8) with triethyl orthoformate leads to the formation Stetter und Steffens Jahrg. 105

Design and sterospecific synthesis of modular ligands based upon cis-1,3-trans-5-substituted cyclohexanes

“…The first target ligand, cis,trans-DAHC (5), was previously synthesised, though not isolated, in 1972 as a by-product in the synthesis of the cis-isomer from 3,5-dinitrophenol. 20 Its diacetamide derivative co-crystallised with the diacetamide of the third, trans-isomer in a combined overall yield of 25%. Although the poor yield is counterbalanced the relatively low cost of the 3,5-dinitrophenol precursor, this method was not considered suitable owing to the difficulty of separating the desired isomer.…”