Synthesis of Novel Organophosphorus Compounds Via Reaction of Substituted 2-oxoindoline-3-ylidene with Acetylenic Diesters and Triphenylphosphine or Triphenyl Phosphite

Overview

Journal Sci Rep

Specialty Science

Date 2024 Mar 16

PMID 38491081

Authors

Mahsa Najafi

Ghasem Marandi

Affiliations

Soon will be listed here.

Abstract

An efficient reaction between triphenylphosphine or triphenyl phosphite and 2-oxoindoline-3-ylidene derivatives in the presence of acetylenic esters leads to functionalized 2-oxoindoline-3-ylidene containing phosphorus ylieds or phosphonate esters. All compounds obtained in these reactions are stable and have good yields.

References

Eldehna W, Abo-Ashour M, Nocentini A, Gratteri P, Eissa I, Fares M . Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino) benzenesulfonamides: Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies. Eur J Med Chem. 2017; 139:250-262. DOI: 10.1016/j.ejmech.2017.07.073. View

Nitti A, Signorile M, Boiocchi M, Bianchi G, Po R, Pasini D . Conjugated Thiophene-Fused Isatin Dyes through Intramolecular Direct Arylation. J Org Chem. 2016; 81(22):11035-11042. DOI: 10.1021/acs.joc.6b01922. View

Gursoy A, Karali N . Synthesis and primary cytotoxicity evaluation of 3-[[(3-phenyl-4(3H)-quinazolinone-2-yl)mercaptoacetyl]hydrazono]-1H-2-indolinones. Eur J Med Chem. 2003; 38(6):633-43. DOI: 10.1016/s0223-5234(03)00085-0. View

Sharma S, Sayyed R, Trivedi M, Gobi T . Phosphate solubilizing microbes: sustainable approach for managing phosphorus deficiency in agricultural soils. Springerplus. 2015; 2:587. PMC: 4320215. DOI: 10.1186/2193-1801-2-587. View

Lai Y, Ma L, Huang W, Yu X, Zhang Y, Ji H . Synthesis and biological evaluation of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors. Bioorg Med Chem Lett. 2010; 20(24):7349-53. DOI: 10.1016/j.bmcl.2010.10.056. View

Efremov A, Beznos O, Eremeev R, Chesnokova N, Milaeva E, Shevtsova E . Microwave-Assisted Synthesis of 3-Hydroxy-2-oxindoles and Pilot Evaluation of Their Antiglaucomic Activity. Int J Mol Sci. 2023; 24(6). PMC: 10049166. DOI: 10.3390/ijms24065101. View

Bal T, Anand B, Yogeeswari P, Sriram D . Synthesis and evaluation of anti-HIV activity of isatin beta-thiosemicarbazone derivatives. Bioorg Med Chem Lett. 2005; 15(20):4451-5. DOI: 10.1016/j.bmcl.2005.07.046. View

Igosheva N, Lorz C, OConner E, Glover V, Mehmet H . Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Neurochem Int. 2005; 47(3):216-24. DOI: 10.1016/j.neuint.2005.02.011. View

Cao Z, Zhou F, Zhou J . Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles. Acc Chem Res. 2018; 51(6):1443-1454. DOI: 10.1021/acs.accounts.8b00097. View

10.

Tisovsky P, Sandrik R, Horvath M, Donovalova J, Filo J, Gaplovsky M . Effect of Structure on Charge Distribution in the Isatin Anions in Aprotic Environment: Spectral Study. Molecules. 2017; 22(11). PMC: 6150331. DOI: 10.3390/molecules22111961. View

11.

Eremeev R, Beznos O, Efremov A, Chesnokova N, Lozinskaya N . The rational design of novel 5-amino-2-oxindole derivatives with antiglaucomic activity. Bioorg Med Chem Lett. 2023; 90:129334. DOI: 10.1016/j.bmcl.2023.129334. View

12.

Zheng H, Han Y, Sun J, Yan C . Tri(-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]. Beilstein J Org Chem. 2022; 18:669-679. PMC: 9235906. DOI: 10.3762/bjoc.18.68. View

13.

Karali N, Gursoy A, Kandemirli F, Shvets N, Kaynak F, Ozbey S . Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg Med Chem. 2007; 15(17):5888-904. DOI: 10.1016/j.bmc.2007.05.063. View

14.

Mansour H, El-Wahab H, Ali A, Aboul-Fadl T . Inversion kinetics of some / 3-(benzylidene)-2-oxo-indoline derivatives and their CDK2 docking studies. RSC Adv. 2022; 11(14):7839-7850. PMC: 8695066. DOI: 10.1039/d0ra10672k. View

15.

Zhang W, Go M . Functionalized 3-benzylidene-indolin-2-ones: inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity. Bioorg Med Chem. 2009; 17(5):2077-90. DOI: 10.1016/j.bmc.2008.12.052. View

16.

Mudithanapelli C, Vasam C, Vadde R, Kim M . Highly Efficient and Practical N-Heterocyclic Carbene Organocatalyzed Chemoselective N/C-Functionalization of Isatins with Green Chemistry Principles. ACS Omega. 2019; 3(12):17646-17655. PMC: 6643579. DOI: 10.1021/acsomega.8b02361. View

17.

Verma M, Pandeya S, Singh K, Stables J . Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharm. 2004; 54(1):49-56. View

18.

Sridhar S, Ramesh A . Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biol Pharm Bull. 2001; 24(10):1149-52. DOI: 10.1248/bpb.24.1149. View

19.

Varun , Sonam , Kakkar R . Isatin and its derivatives: a survey of recent syntheses, reactions, and applications. Medchemcomm. 2019; 10(3):351-368. PMC: 6438150. DOI: 10.1039/c8md00585k. View

20.

Reddy C, Ganesh V, Singh A . - isomerization of 3-benzylidene-indolin-2-ones using a microfluidic photo-reactor. RSC Adv. 2022; 10(48):28630-28634. PMC: 9055887. DOI: 10.1039/d0ra05288d. View