Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds

• Published in: Organic & biomolecular chemistry Vol. 18; no. 34; pp. 671 - 6715
• Main Authors: Rapelli, Chandrashekhar, Sridhar, Balasubramanian, Subba Reddy, B. V
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 14.09.2020; Royal Society of Chemistry
• Subjects: Chemistry; Chemistry, Organic; Crystallography; Cyclization; Indoles; Indoles - chemical synthesis; Indoles - chemistry; Molecular Structure; NMR; Nuclear magnetic resonance; Physical Sciences; Scaffolds; Science & Technology; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; Synthesis; DERIVATIVES; ONE-POT; CONSTRUCTION; FRAMEWORKS
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d0ob01384f

A novel strategy has been developed for the synthesis of indole fused spiro-1,4-diazocane derivatives. Using a tandem Prins cyclization, this is the first report on the synthesis of eight-membered spirodiazocane scaffolds, which are less accessible due to ring strain but more relevant to drug discovery. A tandem Prins strategy has been developed for the first time to produce a novel class of spiro-1,4-diazocane derivatives by the condensation of indole tethered γ-hydroxyolefin with aldehydes using BF 3 ·OEt 2 at −40 °C in dichloromethane.