Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2022 May 28

PMID 35630538

Authors

Kaikai Wang

Yanli Li

Wei Zhang

Rongxiang Chen

Xueji Ma

Mingyue Wang

Nan Zhou

Affiliations

Soon will be listed here.

Abstract

A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and easy to handle. Moreover, a gram-scale experiment further highlights the synthetic utility. The chemical structure of the product was determined by X-ray single-crystal structure analysis. A possible mechanism for this transformation is proposed to explain the reaction process.

Citing Articles

Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines.

Wang K, Zhou W, Jia J, Ye J, Yuan M, Yang J Molecules. 2023; 28(19).

PMID: 37836604 PMC: 10574269. DOI: 10.3390/molecules28196761.

References

Worayuthakarn R, Thasana N, Ruchirawat S . Three distinct reactions of 3,4-dihydroisoquinolines with azlactones: novel synthesis of imidazoloisoquinolin-3-ones, benzo[a]quinolizin-4-ones, and benzo[d]azocin-4-ones. Org Lett. 2006; 8(25):5845-8. DOI: 10.1021/ol062429m. View

Zhou X, Xu X, Shi Z, Liu K, Gao H, Li W . Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: direct access to 3,4,5-trisubstituted isoxazoles. Org Biomol Chem. 2016; 14(23):5246-50. DOI: 10.1039/c6ob00717a. View

Srivastava R . Mass spectrometric analysis of 1,2,4-oxadiazoles and 4,5-dihydro-1,2,4-oxadiazoles. Mass Spectrom Rev. 2004; 24(3):328-46. DOI: 10.1002/mas.20017. View

Bhat S, Robinson D, Moses J, Sharma P . Synthesis of Oxadiazol-5-imines via the Cyclizative Capture of in Situ Generated Cyanamide Ions and Nitrile Oxides. Org Lett. 2016; 18(5):1100-3. DOI: 10.1021/acs.orglett.6b00203. View

Mercalli V, Massarotti A, Varese M, Giustiniano M, Meneghetti F, Novellino E . Multicomponent Reaction of Z-Chlorooximes, Isocyanides, and Hydroxylamines as Hypernucleophilic Traps. A One-Pot Route to Aminodioximes and Their Transformation into 5-Amino-1,2,4-oxadiazoles by Mitsunobu-Beckmann Rearrangement. J Org Chem. 2015; 80(19):9652-61. DOI: 10.1021/acs.joc.5b01676. View

Schafer R, Monaco M, Li M, Tirla A, Rivera-Fuentes P, Wennemers H . The Bioorthogonal Isonitrile-Chlorooxime Ligation. J Am Chem Soc. 2019; 141(47):18644-18648. DOI: 10.1021/jacs.9b07632. View

Lin H, Snider B . Synthesis of phidianidines A and B. J Org Chem. 2012; 77(10):4832-6. PMC: 3356445. DOI: 10.1021/jo300449n. View

Vo Q, Trenerry C, Rochfort S, Wadeson J, Leyton C, Hughes A . Synthesis and anti-inflammatory activity of aromatic glucosinolates. Bioorg Med Chem. 2013; 21(19):5945-54. DOI: 10.1016/j.bmc.2013.07.049. View

Narayan R, Potowski M, Jia Z, Antonchick A, Waldmann H . Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis. Acc Chem Res. 2014; 47(4):1296-310. PMC: 4004623. DOI: 10.1021/ar400286b. View

10.

Jiang K, Luesakul U, Zhao S, An K, Muangsin N, Neamati N . Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-]indolone Derivatives. ACS Omega. 2018; 2(7):3123-3134. PMC: 6044867. DOI: 10.1021/acsomega.7b00490. View

11.

Zhu J, Ye Y, Ning M, Mandi A, Feng Y, Zou Q . Design, synthesis, and structure-activity relationships of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles as TGR5 agonists. ChemMedChem. 2013; 8(7):1210-23. DOI: 10.1002/cmdc.201300144. View

12.

Bethge K, Pertz H, Rehse K . New oxadiazole derivatives showing partly antiplatelet, antithrombotic and serotonin antagonistic properties. Arch Pharm (Weinheim). 2005; 338(2-3):78-86. DOI: 10.1002/ardp.200400927. View

13.

Jakubec P, Helliwell M, Dixon D . Cyclic imine nitro-Mannich/lactamization cascades: a direct stereoselective synthesis of multicyclic piperidinone derivatives. Org Lett. 2008; 10(19):4267-70. DOI: 10.1021/ol801666w. View

14.

Yi F, Sun Q, Sun J, Fu C, Yi W . Terminal Alkyne-Assisted One-Pot Synthesis of Arylamidines: Carbon Source of the Amidine Group from Oxime Chlorides. J Org Chem. 2019; 84(11):6780-6787. DOI: 10.1021/acs.joc.9b00538. View

15.

Jarvis C, Jemal N, Knapp S, Seidel D . Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins. Org Biomol Chem. 2018; 16(23):4231-4235. PMC: 6082175. DOI: 10.1039/c8ob01015c. View

16.

Zhao G, Liang L, Wen C, Tong R . In Situ Generation of Nitrile Oxides from NaCl-Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition. Org Lett. 2018; 21(1):315-319. DOI: 10.1021/acs.orglett.8b03829. View

17.

Zhang F, Wang Y, Chiba S . Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones. Org Biomol Chem. 2013; 11(36):6003-7. DOI: 10.1039/c3ob41393d. View

18.

Ferwanah A, Awadallah A . Reaction of nitrilimines and nitrile oxides with hydrazines, hydrazones and oximes. Molecules. 2007; 10(2):492-507. PMC: 6147710. DOI: 10.3390/10020492. View

19.

Elliott M, Williams E . Synthesis and reactions of partially reduced biisoquinolines. Org Biomol Chem. 2003; 1(17):3038-47. DOI: 10.1039/b306159k. View

20.

Zhu Z, Lv X, Anesini J, Seidel D . Synthesis of Polycyclic Imidazolidinones via Amine Redox-Annulation. Org Lett. 2017; 19(23):6424-6427. PMC: 5715285. DOI: 10.1021/acs.orglett.7b03309. View