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Zenichi Yoshida (1925-2023)
Zenichi Yoshida (1925-2023)
Professor. Zenichi Yoshida,
a member of the Honorary Advisors of HETEROCYCLES (1975-1998),
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Kunio Ogasawara
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Paper | Regular issue | Vol 51, No. 9, 1999, pp.2065-2072
Published online, 1st January, 1970■ Asymmetric Synthesis of Octahydro-2H-pyrido[1,2-a]pyrazines
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8544
■ 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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