Design and synthesis of polycyclic bisindoles via Fischer indolization and ring-closing metathesis as key steps. Issue 50 (14th December 2016)

• Record Type: Journal Article
• Authors: Kotha, Sambasivarao; Cheekatla, Subba Rao; Chinnam, Ajay Kumar; Jain, Tanu
• Is Part Of: Tetrahedron letters. Volume 57:Issue 50(2016)
• Page Start: 5605
• Page End: 5607
• Publication Date: 2016-12-14
• Subjects: Cookson's dione -- Aza ployquinanes -- Polycyclic bisindoles -- Low melting mixtures -- Fisher indolization -- Olefin-metathesis -- Green chemistry -- Deep eutectic media; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.10.112
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthesized various polycyclic bisindoles via Fisher indolization. Fisher indolization was achieved under deep eutectic media. RCM is used for designing aza-polyquinanes. Atom economic process are employed for bisindole synthesis. Transannular cyclized product was isolated under ZnCl2 conditions. Abstract: Several bisindoles have been synthesized starting with a readily available tetracyclic dione via Fischer indolization and ring-closing metathesis as key steps. The Fischer indolization was achieved under deep eutectic reaction conditions using l -tartaric acid and dimethyl urea (30:70). Various indole derivatives synthesized here are C 2 -symmetrical in nature. Due to binding ability, most of the C 2 -symmetrical indole moieties exhibit inhibitory activities against to HIV-1 protease, Gram-positive bacteria Bacillus subtilis and Micrococcus luteus . These C 2 -symmetric new chemical entities play a special role in medicinal chemistry.