A domino reaction of tetrahalo-7, 7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives. Issue 1 (4th November 2014)

• Record Type: Journal Article
• Authors: Raveendra Babu, Kaki; Ahmed Khan, Faiz
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 1(2015)
• Page Start: 299
• Page End: 308
• Publication Date: 2014-11-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob01977f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An acid mediated synthesis of indenones and a de novo synthesis of ninhydrin derivatives. Abstract : An efficient acid induced rearrangement of a tetrahalo-7, 7-dimethoxybicyclo[2.2.1]heptenyl system leading to substituted indenones is reported. This domino reaction involves dehydration, olefin isomerization, ketal hydrolysis, [3, 3]-sigmatropic rearrangement and dehydrohalogenation. The resultant vicinal dihalo olefin moiety in the efficiently generated indenone derivatives was utilized to transform into ninhydrin derivatives by employing Ru(iii )-catalyzed oxidation.