A Concise Synthesis to Benzo[c]cinnolines via 2, 2'‐Dinitro‐1, 1'‐Biphenyls Attained from a Novel Tailored Suzuki Cross‐Coupling. Issue 29 (12th October 2017)

• Record Type: Journal Article
• Authors: Elumalai, Vijayaragavan; Bjørsvik, Hans‐René
• Is Part Of: ChemistrySelect. Volume 2:Issue 29(2017)
• Page Start: 9387
• Page End: 9390
• Publication Date: 2017-10-12
• Subjects: Benzo[c]cinnoline -- 2, 2'-Dinitro-1, 1'-biphenyl -- N- heterocycle -- Palladium -- Suzuki cross-coupling; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201701993
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A new two‐step synthetic process for the preparation of unsymmetrically substituted benzo[ c ]cinnolines was developed. The key intermediate 2, 2'‐dinitro‐1, 1'‐biphenyl was prepared by means of an unprecedented tailored Suzuki cross‐coupling protocol. The subsequent step is constituted by a domino partial nitro group reduction and intramolecular diazo bond formation, a process that afford target benzo[ c ]cinnoline scaffold. The disclosed method tolerates both electron‐withdrawing‐ and electron‐donating groups. Abstract : Access to unsymmetrically substituted benzo[ c ]cinnolines were achieved by means of a unprecedented tailored Suzuki cross‐coupling protocol that allows production of un‐symmetrically substituted 2, 2'‐dinitro‐1, 1'‐biphenyls. The continuation of the overall process consists of a significantly improvement of a domino partial nitro group reduction and intramolecular diazo bond formation process that produce target scaffold benzo[ c ]cinnoline in a microwave assisted step.