Tetrahedron ( IF 2.1 ) Pub Date : 2023-01-21 , DOI: 10.1016/j.tet.2023.133277
Akın Akıncıoğlu , Yusuf Akbaba , Leyla Polat Köse , Leyla Demirkol Akyüz , Süleyman Göksu
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We performed the racemic synthesis and asymmetric resolution of one 2-aminoindane and three 2-aminotertalins due to their crucial biological roles in the central nervous system (CNS). For this reason, desired (±)-2-aminoindane and (±)-2-aminotetralin derivatives were synthesized starting from appropriate reagents. While highly enantio pure (+)-39, (+)-40, and (−)-40 were obtained from the reaction of racemic amines with (R)-O-acetylmandeloyl chloride followed by crystallization, hydrolysis with KOH and acidification with HCl, (S)-42 and (−)-43 were synthesized via the reaction of racemic amines with (S)-mandelic acid and hydrolysis.
中文翻译:

取代的2-氨基茚满和2-氨基四氢萘衍生物的合成及不对称拆分
由于它们在中枢神经系统 (CNS) 中的重要生物学作用,我们对一种 2-氨基茚满和三种 2-氨基特他林进行了外消旋合成和不对称拆分。为此,从适当的试剂开始合成了所需的 (±)-2-氨基茚满和 (±)-2-氨基四氢萘衍生物。而高对映体纯 ( + ) -39、 ( + ) -40和 ( − ) -40是由外消旋胺与 (R)-O-乙酰扁桃酰氯反应,然后结晶,用 KOH 水解和用 HCl 酸化得到的, ( S )- 42和 (−)- 43通过外消旋胺与 (S)-扁桃酸的反应和水解合成。