Facile Preparation of Benzo[4,5]thieno[2,3-b]pyridines and Naphtho[b-4,5]thieno[2,3-b]pyridines via the Reaction of Barton Esters and Benzynes

• Published in: Journal of organic chemistry Vol. 67; no. 10; pp. 3409 - 3411
• Main Authors: Rao, U. Narasimha, Biehl, Ed
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.05.2002; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; INVENTION; RADICAL REACTIONS; Diazotization; One pot reaction; Ester; Cycloaddition; Sulfur heterocycle; Thione; Nitrogen heterocycle; Aryne; Anthranilic acid derivatives; Tricyclic compound; Chemical synthesis; Pyridine derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo016407j

Titled compounds were prepared in a one-pot synthesis by generating symmetrically substituted benzyne intermediates by the diazotization of anthranilic acids in the presence of Barton esters. Unsymmetrically substituted aryne either gave mixtures of regioisomers or failed. However, nitro and methyl derivatives of titled compounds could be obtained as single products using appropriately substituted Barton esters.