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Palladium‐Catalyzed Synthesis of 6 H ‐Dibenzo[ c,h ]chromenes and 5,6‐Dihydrobenzo[ c ]phenanthridines: Application to the Synthesis of Dibenzo[ c,h ]chromene‐6‐ones, Benzo[ c ]phenanthridines, and Arnottin I
Author(s) -
Pramanik Subhendu,
Jash Moumita,
Mondal Debasmita,
Chowdhury Chinmay
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900833
Subject(s) - chemistry , intramolecular force , palladium , catalysis , aldehyde , nucleophile , medicinal chemistry , domino , stereochemistry , cascade reaction , combinatorial chemistry , organic chemistry
6 H ‐Dibenzo[ c,h ]chromenes and 5,6‐dihydrobenzo[ c ]phenanthridines have been synthesized via Palladium (II)‐catalyzed domino reactions of acetylenic substrates involving intramolecular trans ‐oxo/amino palladation onto the triple bond followed by nucleophilic addition of the intermediate to a tethered cyano/aldehyde. The scope of this reaction was extended through one step conversion of some of the products to 6 H ‐dibenzo[ c,h ]chromen‐6‐ones and benzo[ c ]phenanthridines. Utilization of this methodology led to a formal total synthesis of the natural product Arnottin I .