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- W2014501654 abstract "Die Ester 3a und 4a der Benzimidazol-carbonsäure-(2) bzw. Imidazol-dicarbonsäure-(4.5) reagieren mit Isocyanaten zu den offenkettigen Addukten 3b und 4b, die in Gegenwart basischer Katalysatoren nicht cyclisieren. 4a bildet jedoch mit Methylisocyanat und äthanolischer Kalilauge direkt das noch unbekannte 1.5-Imidazol-dicarboximid-System 51). Die Ester von Prolin und Pipecolinsäure (6a bzw. 8a) liefern unter ähnlichen Bedingungen über die offenkettigen Addukte 6b und 8b die 1.2-Pyrrolidin- bzw. 1.2-Piperidin-dicarboximide 7 bzw. 92). — Isatin (10a) reagiert mit Isothiocyanaten in Gegenwart von Äthanol/Triäthylamin direkt zu den Tetrahydrochinazolinen 14a, b; 14b. sowie sein bekanntes O-Analogon 12a3) tauschen beim Versuch der Carbamoylierung mit Methylisocyanat/Triäthylamin OH gegen NHCH3 aus, wobei 15 bzw. 13 gebildet werden. Isatin-3-imid (lla) bildet mit Isocyanaten die Dicarbamoyl-Derivate lib, c, die mit Äthanol/Triäthylamin in die Spiro-[chinazolin-4.4′-hydantoine] 18a, b übergehen, deren System noch nicht beschrieben ist1). Heterocyclizations, VII. New Hydantoins with Bridge-head Nitrogen or Spiran Structure The esters 3a and 4a of benzimidazole-2-carboxylic acid and imidazole-4,5-dicarboxylic acid add isocyanates to give the acyclic adducts 3b and 4b, resp., which do not undergo cyclization, in the presence of basic catalysts. However, 4a forms with methyl isocyanate and ethanolic potassium hydroxide directly the hitherto unknown 1,5-imidazole dicarboximide system 51) Under similar conditions the esters of proline and pipecolinic acid (6a, 8a) give via the acyclic derivatives 6b and 8b the 1,2-pyrrolidine dicarboximide 7 or 1,2-piperidine dicarboximide 92), resp. — Isatin (10a) reacts with isothiocyanates in the presence of ethanol/triethylamine directly to give the tetrahydroquinazolines 14a, b; these as well as their already known O-analogue 12a3), when treated with methylisocyanate/triethylamine, exchange OH for NHCH3 and form 15 or 13, resp. Isatin-3-imide (lla) gives with isocyanates the dicarbamoyl derivatives 11b, c, which are converted by ethanol/triethylamine into the spiro[quinazoline-4,4′-hydantoins] 18a, b, whose system has not yet been described1)." @default.
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- W2014501654 date "1970-08-01" @default.
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- W2014501654 title "Heterocyclisierungen, VII Neue Hydantoine mit Brückenkopf‐Stickstoff bzw. Spiran‐Struktur" @default.
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- W2014501654 doi "https://doi.org/10.1002/cber.19701030810" @default.
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