Synthesis a new derivatives of benzoxazole
Using phosphoric acid and phosphor pent oxide as new catalyst for preparing of derivatives of benzoxazole. Use of benzoaxol ring in medicinal chemistry. Synthesis of 1,3-(Benzene-1,3-diyl) bis(benzoxazole). Synthesis of 3-(2-Hydroxynaphthol) benzoxazole.
| Рубрика | Химия |
| Вид | статья |
| Язык | английский |
| Дата добавления | 21.01.2021 |
| Размер файла | 395,8 K |
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Al-Baath University
SYNTHESIS A NEW DERIVATIVES OF BENZOXAZOLE
Hasan Abu Jarra, 3rd years PHD student
Rushdi Madwar, Pro. Assistant
Joumaa Merza, Professor of Natural Products
Homs, Syria
Аннотация
Хасан Абу Джарра, аспирант 3-го курса Рушди Мадвар, Pro. Ассистент, Джумаа Мерза Профессор натуральных продуктов Хомс, Сирия Университет Аль-Баас
СИНТЕЗ НОВЫХ ПРОИЗВОДНЫХ БЕНЗОКСАЗОЛА
Три производных бензоксазола (BNXS) были приготовлены с использованием оксида фосфорной кислоты / фосфорной кислоты в качестве нового катализатора. Соответствующие карбоновые кислоты смешивали с 2-аминофенолом с получением параллельных производных бензоксазолов. Спектроскопические методы, такие как ИК, 1Н-ЯМР и 13CINMR, использовали для спецификации полученных соединений.
Ключевые слова: бензоксазол, бензтиазол, флуоресценция.
Annotation
Three derivatives of Benzoxazole (BNXs) have been prepared using Phosphoric Acid /Phosphor Pent oxide as new catalyst. Appropriate carboxylic acids were mixed with 2-Aminophenol produce the parallel Benzoxazoles derivatives. Spectroscopic techniques like IR, Experimental
2.1. Materials and methods
1.1General
All pure reagent materials were purchased from inveterate companies like BDH, Merck and Sigma Aldrich. The FT-IR spectra were recorded on Jasco spectrometer using KBr discs. 1H NMR and 13C NMR spectra recorded on 400-MHz Bruker spectrometer using TMS as internal standard. Fluorescence spectra achieved using Shimadzo RF-530 1PC spectrofluormeter using chloroform as solvent. Synthesis of Benzoxazole derivatives 2.1General procedure for synthesis (BNXs) derivatives All synthesized products were prepared according to scheme (1).H-NMR & 13CINMR were used to specification prepared compounds.
Keywords: Benzoxazole, Benzthiazole, Fluorescence.
Introduction
A heterocyclic compounds are compounds that possess a cyclic structure with at least two different kinds of heteroatoms in their ring. Nitrogen, oxygen, and sulfur are the most common heteroatoms[1, C. 209]. Oxygen heterocyclic compounds form an important class in organic chemistry, especially those fused to benzene ring [2, C. 12577]. Furthermore, compounds with thiazole ring have great value in medicinal field, in addition to their responsibility for variety of biological activities[3,C. 12301]. Benzoxazole ring is one of the most common heterocyclic in medicinal chemistry, it has remarkable biological and photochromic activities like antihypertensive, antimicrobial, antiviral, antifungal, anticancer, antihistamine, antihelminthic, antiparasitic, anticoagulant, in addition to their herbicidal and insecticidal activities[4,C. 3247]. Because of their optical applications, like
photoluminescents, whitening agents and dye laser, (BNXS), have gained special attention. Furthermore, metal complexes of their hydroxy substituted derivatives are used as luminescent materials for Organic Light-Emitting Diodes (OLEDS) and sensors for the metals detection[5,C. 339].
Synthesis of 1,3-(Benzene-1, 3-diyl) bis(benzoxazole) (5)
Isophathlic acid (1) (5 mmol) and 2-Aminophenl (4) (10 mmol) were taken in (50 mL) flask contain (10 mL) of preheated catalyst (H3PO4/P2O5). The obtained product has yellowish White color, mp (°C) 216-217, yield (%) 76.76; IR (Cm-1) figure (1): 3056 (vAr-H str), 1618 (vc=n- str); 1H NMR (CDC13, 400 MHz) 5 (ppm) figure (2): 9.17 (s, 1H), 8.53 (d, J=, 2H), 8.36 (d, J=, 2H), 7.78 (d, J=, 4H), 7.29 (m, J=, 3H); 13C NMR (CDC13, 100 MHz) 5 (ppm) figure (3): 162.08, 150.92, 142.08,
Synthesis of 2,6-(Pyridine-2,6-diyl) bis(benzoxazole) (6)
2,6-Pyridine dicarboxylic acid (2) (5 mmol) and (4) (10 mmol) were taken in (50 mL) flask contain (10 mL) of preheated catalyst (H3PO4/P2O5. Pink color product was obtained, mp (°C) 270-271, yield (%) 23.53; IR (Cm-1) figure (4) 3056 (vai-h str), 1614 (vc=n- str); XH NMR (CDCl3, 400 MHz) 5 (ppm) figure (5): 8.47 (d, J=8, 2H), 8.13 (d, J=8, 2H), 8.00 (m, 3H), 7.53 (ddd,J1=8, J2=4, 2H), 7.45 (ddd,J1=8, J2=4, 2H); 13C NMR (CDCl3, 100 MHz) 5 (ppm) figure (6): 168.62, 154.08,
Synthesis of 3-(2-Hydroxynaphthol) benzoxazole (6)
chemistry phosphoric benzoxazole medicinal
Figure (7) IR spectra of 3-(2-Hydroxynaphthol) benzoxazole
Figure (8) H NMR spectra of of 3-(2-Hydroxynaphthol) benzoxazole
Figure (9) 13C NMR spectra of of 3-(2-Hydroxynaphthol) benzoxazole
3-(2-Hydroxynaphthoic) acid (3) (10 mmol) and 2-Aminophenl (4) (10 mmol) were added into ( 50 mL) flask contain (10 mL) of preheated catalyst (H3PO4/P2O5). A slightly yellowish product has obtained. mp (°C) 154-155, yield (%) 85.04; IR (Cm-1) figure (7) 3442 (vo-h str), 3041 (vai-h str), 1644 (vc=n- str); 1H NMR (CDCl3, 400 MHz) 5 (ppm) figure (8): 11.27 (s, 1H), 8.60 (s, 1H), 7.86 (d, J=8 Hz, 1H), 7.73 (dd, J=19 Hz, 8.4 Hz, 2H), 7.64(d, J=5.2 Hz, 1h), 7.48 (t, J=8, 1H), 7.41 (m, 3H) 7.34 (t, J= 8 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 5 (ppm) figure (9): 162.52, 154.27, 149.34, 140.13, 136.73, 128.70, 128.63, 128.45, 127.49, 126.52, 125.82, 125.18, 124.04, 119.57, 112.67, 111.65, 110.73.
Results and discussion
A new derivatives of (BNXs) & (BNTs) have been synthesized using laboratory prepared mixed catalyst of phosphoric acid and phosphorus pent oxide.
References
1. P. S. Monitor, “Impact factor: 0.3397/ICV: 4.10,” vol. 5, no. 1, pp. 207-225, 2014.
2. H. Miyabe, “Synthesis of oxygen heterocycles via aromatic C-O bond formation using arynes,” Molecules, vol. 20, no. 7, pp. 12558-12575, 2015.
3. D. Leonte, L. C. Bencze, C. Paizs, F. D. Irimie, and V. Zaharia, “Heterocycles 38. Biocatalytic synthesis of new heterocyclic mannich bases and derivatives,” Molecules, vol. 20, no. 7, pp. 12300-12313, 2015.
4. K. Tao, J. Zheng, Z. Liu, W. Shen, and J. Zhang, “Facile synthesis of benzoxazoles from 1,1-dibromoethenes,” Tetrahedron Lett., vol. 51, no. 24, pp. 3246-3249, 2010.
5. S. Mao, H. Zhang, K. Shen, Y. Xu, X. Shi, and H. Wu, “Three different configurations of d10complexes based on benzoxazole pyridyl ligand: Synthesis, structures and properties,” Polyhedron, vol. 134, pp. 336-344, 2017.
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