N. N. Mochulskaya, A. A. Andreiko, V. N. Charushin, B. V. Shulgin, D. V. Raikov, V. I. Solomonov, “Intermolecular and intramolecular cycloaddition reactions of 1-ethyl-1,2,4-triazinium salts with alkynes”, Mendeleev Commun., 2001, Volume 11, Issue 1,Pages <nobr>19

This article is cited in 7 papers

Intermolecular and intramolecular cycloaddition reactions of 1-ethyl-1,2,4-triazinium salts with alkynes

N. N. Mochulskaya^a, A. A. Andreiko^a, V. N. Charushin^b, B. V. Shulgin^b, D. V. Raikov^b, V. I. Solomonov^a

^a Urals State Technical University, Ekaterinburg, Russian Federation
^b Department of Organic Chemistry, Urals State Technical University, Ekaterinburg, Russian Federation

Abstract: Azomethyne ylides generated from 3-alkylthio substituted 1-alkyl-5-aryl-1,2,4-triazinium salts 4a–c on treatment with triethylamine undergo 1,3-dipolar cycloaddition with dimethyl acetylenedicarboxylate to give pyrrolo[2,1-f] [1,2,4]triazines, while 1-ethyl-5- phenyl-1,2,4-triazinium salts 1a,b bearing the C≡C bond in the side-chain 3-alkynylthio substituent react with acetylenes to undergo either intermolecular 1,3-dipolar cycloaddition or intramolecular inverse electron demand Diels–Alder reactions.

Language: English

DOI: 10.1070/MC2001v011n01ABEH001370