N-alkyl imidazole-based homonuclear coordination complex as a neutral organocatalyst for the faster and efficient construction of 3,4-dihydro-2H-1,3-oxazine scaffold

被引:3
作者
Yildirim, Ayhan [1 ]
Goker, Mustafa [1 ]
机构
[1] Bursa Uludag Univ, Fac Arts & Sci, Dept Chem, POB 16059, Bursa, Turkey
关键词
1; 3-benzoxazines; metal complex catalyst; multicomponent synthesis; N-alkylimidazole; two-component synthesis; BENZOXAZINE; DERIVATIVES; CHAIN; CO2;
D O I
10.1002/aoc.6425
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In the present work, homonuclear coordination complex including Zn (II) and N-hexadecylimidazole ligand was used for the first time as a highly efficient homogeneous neutral organocatalyst for the synthesis of 3,4-dihydro-2H-1,3-benzoxazine monomers. Therefore, N-alkyl or N-aryl substituted, both mono-benzoxazine and bis-benzoxazine, were successfully synthesized (21 examples) via Mannich-type condensation reactions. Effortlessly obtaining the pure product with high yields and the short reaction time makes this method more useful and advantageous than the common existing benzoxazine synthesis methods.
引用
收藏
页数:12
相关论文
共 45 条
[1]   Synthesis of 3,4-dihydro-2H-1,3-benzoxazines by condensation of 2-hydroxyaldehydes and primary amines: Application to the synthesis of hydroxy-substituted and deuterium-labeled compounds [J].
Andreu, R. ;
Ronda, J. C. .
SYNTHETIC COMMUNICATIONS, 2008, 38 (14) :2316-2329
[2]   Design and functionalization of bioactive benzoxazines. An unexpected ortho-substitution effect [J].
Arendt-Pindel, Agata ;
Marszalek-Harych, Aleksandra ;
Gebarowska, Elzbieta ;
Gebarowski, Tomasz ;
Jedrzkiewicz, Dawid ;
Plaskowska, Elzbieta ;
Zalewski, Dariusz ;
Gulia, Nurbey ;
Szafert, Slawomir ;
Ejfler, Jolanta .
NEW JOURNAL OF CHEMISTRY, 2019, 43 (30) :12042-12053
[3]   Effects of a Flexible Alkyl Chain on a Ligand for CuAAC Reaction [J].
Asano, Keisuke ;
Matsubara, Seijiro .
ORGANIC LETTERS, 2010, 12 (21) :4988-4991
[4]   Amphiphilic Organocatalyst for Schotten-Baumann-Type Tosylation of Alcohols under Organic Solvent Free Condition [J].
Asano, Keisuke ;
Matsubara, Seijiro .
ORGANIC LETTERS, 2009, 11 (08) :1757-1759
[5]  
Attanasi OA, 2012, CURR ORG CHEM, V16, P2613
[6]   Bio-based benzoxazines synthesized in a deep eutectic solvent: A greener approach toward vesicular nanosystems [J].
Behalo, Mohamed S. ;
Bloise, Ermelinda ;
Mele, Giuseppe ;
Salomone, Antonio ;
Messa, Francesco ;
Carbone, Luigi ;
Mazzetto, Selma Elaine ;
Lomonaco, Diego .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (02) :768-773
[7]   Novel Benzoxazine-Based Aglycones Block Glucose Uptake In Vivo by Inhibiting Glycosidases [J].
Bharathkumar, Hanumantharayappa ;
Sundaram, Mahalingam S. ;
Jagadish, Swamy ;
Paricharak, Shardul ;
Hemshekhar, Mahadevappa ;
Mason, Daniel ;
Kemparaju, Kempaiah ;
Girish, Kesturu S. ;
Basappa ;
Bender, Andreas ;
Rangappa, Kanchugarakoppal S. .
PLOS ONE, 2014, 9 (07)
[8]   Synthesis and characterization of imidazolium telechelic poly(butylene terephthalate) for antimicrobial applications [J].
Colonna, Martino ;
Berti, Corrado ;
Binassi, Enrico ;
Fiorini, Maurizio ;
Sullalti, Simone ;
Acquasanta, Francesco ;
Vannini, Micaela ;
Di Gioia, Diana ;
Aloisio, Irene ;
Karanam, Sreepadaraj ;
Brunelle, Daniel J. .
REACTIVE & FUNCTIONAL POLYMERS, 2012, 72 (02) :133-141
[9]   Influence of substituent on equilibrium of benzoxazine synthesis from Mannich base and formaldehyde [J].
Deng, Yuyuan ;
Zhang, Qin ;
Zhou, Qianhao ;
Zhang, Chengxi ;
Zhu, Rongqi ;
Gu, Yi .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2014, 16 (34) :18341-18348
[10]   Oxazine Ring-Related Vibrational Modes of Benzoxazine Monomers Using Fully Aromatically Substituted, Deuterated, 15N Isotope Exchanged, and Oxazine-Ring-Substituted Compounds and Theoretical Calculations [J].
Han, Lu ;
Iguchi, Daniela ;
Gil, Phwey ;
Heyl, Tyler R. ;
Sedwick, Victoria M. ;
Arza, Carlos R. ;
Ohashi, Seishi ;
Lacks, Daniel J. ;
Ishida, Hatsuo .
JOURNAL OF PHYSICAL CHEMISTRY A, 2017, 121 (33) :6269-6282