Synthesis of 1,1-Dialkylindolium-2-thiolates via Base-Induced Transformation of 4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole in the Presence of Secondary Amines
- 9 October 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (21) , 8612-8614
Abstract
4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole undergoes ring-opening to produce a thioketene intermediate that reacts with secondary amines forming 2-(2-chloro-5-nitrophenyl)-N,N-dialkylthioacetamides. Intramolecular cyclization of these thioamides via nucleophilic substitution of the halogen on the aromatic ring affords nonaromatic 1,1-dialkylindolium-2-thiolates instead of the expected aromatic N,N-dialkylaminobenzo[b]thiophenes.Keywords
This publication has 8 references indexed in Scilit:
- Synthesis and Reactivity of 4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole. A Novel One-pot Synthesis of N-Substituted Indole-2-thiolsThe Journal of Organic Chemistry, 2007
- One-Pot Synthesis of Substituted 2-Aminobenzo[b]thiophenesThe Journal of Organic Chemistry, 2007
- Synthesis and anti-tyrosine kinase activity of 3-(substituted-benzylidene)-1, 3-dihydro-indolin derivatives: investigation of their role against p60c-Src receptor tyrosine kinase with the application of receptor docking studiesIl Farmaco, 2005
- A Solid-Phase Approach to the Phallotoxins: Total Synthesis of [Ala7]-PhalloidinThe Journal of Organic Chemistry, 2005
- Design and synthesis of novel tetra-peptide motilin agonists.Bioorganic & Medicinal Chemistry, 2002
- A Novel Protocol for Construction of Indolylmethyl Group at Aldehydes or KetonesSynlett, 2001
- Efficient synthesis of 3-(4,5-dihydro-1H-imidazole-2-yl)-1H-indolesTetrahedron Letters, 2001
- Replacement of methylthio functions on aromatic heterocycles by hydrogen, alkyl and aryl groups via nickel-induced Grignard reactionsThe Journal of Organic Chemistry, 1985