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October 15, 2019
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Published online, 1st January, 1970
■ Asymmetric Synthesis of Octahydro-2H-pyrido[1,2-a]pyrazines
Olivier Froelich, Françoise Cossart, Martine Bonin, Jean-Charles Quirion,* and Henri-Philippe Husson*
*Laboratoire d'Hétérochimie Organique, Associé au C.N.R.S., IRCOF, INSA de Rouen, Place Emile Blondel, P08, 76131 Mont-Saint-Aignan Cedex, France
Abstract
A series of optically pure octahydro-2H-pyrido[1,2-a]pyrazines has been prepared from (-)-2-cyano-6-phenyloxazolopiperidine (4). 2H-Pyrido[1,2-a]pyrazin-3-(4H)-one (7) and octahydro-2H-pyrido[1,2-a]pyrazine (14) were obtained from diamino alcohol (5) by cyclization of bromo- or chloroamides (6) and (10). (4R,9aS)-1,1,4-Triphenyloctahydro-2H-pyrido[1,2-a]pyrazine (16) was synthesized by cyclization of amino alcohol (15c). The formation of cyclic urea (8aS)-diphenyl-3-oxooctahydroimidazo[1,5-a]pyridine (18) was observed during the hydrogenolysis of the corresponding carbamate (17).
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