Iodide-Catalyzed Selenium-Assisted Sequential Multicomponent Synthesis of a Luminescence Benzo-Oxazino-Isoindole Framework

Abstract

We have described an unexpected pathway using the R-NC/Se system for the synthesis of the unreported benzooxazino-isoindole framework by the iodide-catalyzed selenium-assisted sequential multicomponent reaction of the Knoevenagel adduct of ninhydrin and malononitrile, isocyanide, amine, and elemental selenium under mild reaction conditions. The photophysical properties of the products were investigated by absorption and emission spectroscopy, revealing that the new heterocyclic system has good fluorescence properties.

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

“…Another approach to access chromophores with an isoindole core proceeds via sequential MCR of the Knoevenagel adduct of ninhydrin and malononitrile, isocyanide, amine, and elemental selenium. The iodide-catalyzed process very likely involves a radical ring enlargement and furnishes luminescent benzooxazino-isoindole derivates 41 under mild reaction condition according to the chromophore concept (Scheme 11B) (Sedighian (Sedighian et al, 2021).…”

Ultrasound-promoted synthesis of novel N-arylamino-3,5′-biquinoline derivatives: their applications in live-cell imaging and in vitro anticancer activity evaluation

“…It is well known that the hydrogen bond accepting capabilities of solvents result in dyes having a reduced ground state energy and increased excited state energy, resulting in a blue shift. 32 Scheme 2 Mechanistic rationale for the synthesis of 3.…”

“…Derivatives 3a, 3g, 3h, 3i, and 3j were purified by washing with EtOH twice and the other derivatives 3b, 3c, 3d, 3e, and 3f were purified by recrystallization in DMF. (17), 472 (37), 469 (6), 446 (6), 427 (5), 393 (5), 235 (32), 213 (9), 194 (9), 76 (9), 51 (14) 19) Å 3 , Z = 8, Dc = 1.368 mg m À3 , F (000) = 2096, crystal dimension 0.20 Â 0.15 Â 0.10 mm, radiation, Mo Ka (l = 0.71073 Å), 1.9 r 2y r 25.0, intensity data were collected at 290 K with a Bruker APEX area-detector diffractometer employing a o/2y scanning technique in the range of À32 r h r 32, À9 r k r 9, À26 r l r 24; the structure was solved by direct methods, all non-hydrogen atoms were positioned and anisotropic thermal parameters refined from 4153 observed reflections with R (into) = 0.0499 by a full-matrix least-squares technique converged to R 1 = 0.0668, and wR 2 = 0.1571 [I 4 2sigma(I)].…”

Cellulose-reinforced poly(ethylene-co-vinyl acetate)-supported Ag nanoparticles with excellent catalytic properties: synthesis of thioamides using the Willgerodt–Kindler reaction

“…Several approaches have been used to overcome these limitations. 13–15 The Willgerodt–Kindler reaction has been modified using additives, such as K 2 S 2 O 8 , 16 C 12 H 25 SH, 17 K 3 PO 4 , 10 TsOH, 18 Na 2 S·9H 2 O, 19 K 2 CO 3 , 20 and β-CD, 21 to improve reaction efficiency. Furthermore, environmentally benign reaction conditions have been developed, such as solvent-less and catalyst-free conditions; in addition, water or glycerol was used as the solvent.…”