Microwave assisted synthesis of 2,3-dihydro-4H-benzo[4,5]thiazolo [3,2-a]furo[2,3-d] pyrimidin-4-ones by radical addition of 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a] pyrimidin-4-ones to various conjugated alkenes and dienes mediated Mn(OAc)(3)


YILMAZ M. , Inal A. i. U.

TETRAHEDRON, vol.116, 2022 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 116
  • Publication Date: 2022
  • Doi Number: 10.1016/j.tet.2022.132806
  • Title of Journal : TETRAHEDRON
  • Keywords: Thiazolo[3,2-a]furo[2,3-d]pyrimidin, C-C bond formation, Microwave synthesis, Dihydrofuran, DIVERSITY-ORIENTED SYNTHESIS, CERIUM(IV) AMMONIUM-NITRATE, MANGANESE(III) ACETATE, BIOLOGICAL EVALUATION, 1,3-DICARBONYL COMPOUNDS, FACILE SYNTHESIS, PHOTOLUMINESCENT PROPERTIES, STEREOSELECTIVE-SYNTHESIS, HETEROCYCLIC-COMPOUNDS, OXIDATIVE CYCLIZATION

Abstract

Synthesis of chemically important, novel 2,3-dihydro-4H-benzo [4,5]thiazolo [3,2-a]furo [2,3-d]pyr-imidin-4-one derivatives was approached in this work. These heterocyclic compounds were synthesized in good to excellent yields from the reaction of Mn(OAc)3 mediated radical addition of 2-hydroxy-4H- benzo [4,5]thiazolo [3,2-a]pyrimidin-4-one (1a-1f) derivatives to various conjugated alkenes (2a-2e, 2h) and dienes (2f, 2g, 2i) under microwave irradiation in mild conditions. Also, a different compound skeleton, 2,3-dihydrobenzo [4,5]imidazo [1,2-a]furo [2,3-d]pyrimidin-4(10H)-one 3a (90%), was obtained from the reaction of 2-hydroxy-10-methylbenzo [4,5]imidazo [1,2-a]pyrimidin-4(10H)-one (1g) and 1,1diphenylethylene (2h) for the first time. While no product was obtained with conventional method in radical addition reactions, dihydrofuropyrimidines (3a-z, 3a) were synthesized in excellent yields using microwave irradiating method at 150 ?, 350 W for 60 s. All isolated compounds were characterized by spectroscopic techniques (FTIR, H-1 NMR, C-13 NMR and( 19)F NMR) and HRMS analysis.(c) 2022 Elsevier Ltd. All rights reserved.