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Synthesis of Thieno[3,2‐ e ][1,4]diazepin‐2‐ones: Application of an Uncatalysed Pictet–Spengler Reaction
Author(s) -
Denoyelle Séverine,
Tambutet Guillaume,
Masurier Nicolas,
Maillard Ludovic T.,
Martinez Jean,
Lisowski Vincent
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500943
Subject(s) - diastereomer , pictet–spengler reaction , chemistry , ring (chemistry) , proline , alanine , stereochemistry , phenylalanine , amino acid , organic chemistry , biochemistry
A series of 5‐substituted thieno[3,2‐ e ][1,4]diazepin‐2‐ones was synthesized in four steps from methyl 3‐aminothiophene‐2‐carboxylate. After the coupling of 3‐aminothiophene with α‐amino acids, the key final step that involves an uncatalysed Pictet–Spengler reaction allowed the cyclization of the seven‐membered diazepinone ring. The reaction was first optimized and then exemplified in three different series (phenylalanine, alanine and proline) that led to 24 target diazepinones, which includes 19 optically pure diastereomers.