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Access to a Novel Class of Tetracyclic 1,4‐Benzodiazepin‐5‐ones Starting from α‐Amino Acids by Pd‐Catalyzed Amination/1,3‐Dipolar Cycloaddition as the Key Steps
Author(s) -
Basolo Luca,
Beccalli Egle M.,
Borsini Elena,
Broggini Gianluigi,
Khansaa Maisaa,
Rigamonti Micol
Publication year - 2010
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.200901290
Subject(s) - chemistry , amination , enantiopure drug , intramolecular force , cycloaddition , combinatorial chemistry , 1,3 dipolar cycloaddition , palladium , catalysis , stereochemistry , organic chemistry , enantioselective synthesis
A convenient procedure for the preparation of the novel class of tetracyclic imidazo[2,1‐ c ]pyrazolo[1,5‐ a ][1,4]benzodiazepine‐5,8‐diones is reported. The protocol uses cheap andeasily accessible α‐amino acids as chiral‐pool starting materials and leads to products in an enantiopure form. An intramolecular palladium‐catalyzed amination process to form the imidazole nucleus and an intramolecular 1,3‐dipolar cycloaddition reaction to simultaneously achieve the pyrazole and 1,4‐diazepine rings are the key steps.