Synthesis of 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones and functionalization to triazoles

Author(s)

Ali, Bakhat ; Vasconcelos, Stanley N. S. ; Shamim, Anwar ; Zukerman-Schpector, J. ; Stefani, Helio A.

• Document type: Journal article
• Source: ARABIAN JOURNAL OF CHEMISTRY; v. 10, n. 4, p. 500-508, MAY 2017.
• Web of Science Citations: 0

Abstract

A series of alkynyl maleimides were prepared via one-step cross-coupling reaction using bromomaleimide and acetylenes under the Sonogashira conditions, affording 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones in good to high yields. These products were subsequently converted in the corresponding 1,2,3-triazole using conventional click chemistry approach. The alkynyl maleimide compound (8g) crystallized in the triclinic space group P1 with unit cell parameters a = 5.3692(6), b = 9.2513(10), c = 10.3070(11) angstrom, alpha = 85.349(4), beta = 86.892(4), gamma = 86.892(4)degrees, V = 507.31(10) angstrom(3), and Z = 1. In the crystal the molecules are stacked parallel to the c axis and held together through a C-H...pi and a C-H...O interaction. (C) 2016 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. (AU)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 12/17954-4 - Cyclization reaction of Acetyl- and Ethylpyrrolidin-2-one with Potassium Organotrifluoroborate Salts
• Grantee: Bakhat Ali
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 13/17960-7 - Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura Reaction Using Potassium Organotrifluoroborate salts
• Grantee: Stanley Nunes Siqueira Vasconcelos
• Support Opportunities: Scholarships in Brazil - Doctorate