A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent
Nicolai A Aksenov1, Alexander V Aksenov1, Alexander Kornienko2
1Department of Chemistry, North Caucasus Federal University 1a Pushkin St. Stavropol 355009 Russian Federation naksenov@ncfu.ru.
Abstract:
A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C-C and C-N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Preparation of Nitriles
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane


![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)