Synthesis and Spectroscopic Characterization of a Novel 1, 5-Dibenzodiazepine Derivative

Abstract

Abstract:

Gallium (III) triflate-catalyzed reaction between o-phenylenediamine and ethyl propiolate under solvent-free and ultrasonic irradiation conditions produced a novel 1, 5-benzodiazepine derivative with a yield rate of 88%. Complete assignment of the ¹H and ¹³C NMR chemical shift of the compound was obtained using 2D NMR techniques, including DEPT, ¹H-¹H COSY, ¹H-¹³C HMQC and ¹H-¹³C HMBC. Mass fragmentation pathway was proposed based on the high resolution MS spectrum of the compound.

Key words: NMR, assignment, 2D NMR, TOF MS, 1, 5-benzodiazepine derivative, Ga(OTf)₃

CLC Number:

O482.53
O641

WANG Lu, PAN Xiang-Qiang, CAI Jing-Jing, ZU Jian-Ping. Synthesis and Spectroscopic Characterization of a Novel 1, 5-Dibenzodiazepine Derivative[J]. Chinese Journal of Magnetic Resonance, 2011, 28(3): 383-389.

References

[1] Schutz H. Benzodiazepines[M]. Heidelberg: Springer Press，1982.

[2] Randall L O，Kappel B. Benzodiazepines[M]. New York: Raven Press，1973.

[3] Aversa M C，Ferlazzo A，Gionnetto P，et al. A convenient synthesis of novel[1，2，4]Triazolo[4，3α][1，5]benzodiazepine Derivatives[J]. Synthesis，1986: 230.

[4] Balakrishna M S，Kaboundin B. A simple and new method for the synthesis of 1，5- benzodiazepine derivatives on a solid surface
[J]. Tetrahedron Lett，2001，42: 1 127-1 129. 

[5] Du Y Y，Tian F L，Zhao W Z. [BPy]HSO₄acidic ionic liquid as a novel，efficient and environmentally benign catalyst for synthesis of 1，5-benzodiazepines under mild conditions[J]. Synthetic Commun，2006，36: 1 661-1 669.

[6] Pan Xiang-iang(潘向强)，Zou Jian-ing(邹建平)，Huang Zhi-ao(黄智豪)，et al. Ga(OTf)₃-promoted condensation reactions for 1，5benzodiazepines and 1，5-benzothiazepines[J]. Tetrahedron Lett, 2008，49: 5 302-5 308.

[7] Yuan Jin-wei(袁金伟)，Chen Xiao-lan(陈晓岚)，Qu Ling-bo(屈凌波)，et al. Spectroscopic Characterization of a Novel quinoline-4-phosphoramidate derivative（一种新型的喹啉-4-氨基磷酸酯衍生物的波谱学研究）[J]. Chinese J Magn Reson(波谱学杂志)，2009，26(1): 95-102.

[8] Zhang Pei-xuan(张佩璇)，Li Jian-feng(李剑峰)，Wei Ya-bing(韦亚兵)，et al. NMR Characterization and structural elucidation of fluorine derivative of Tetrahydroberberine(氟代四氢小檗碱的波谱特征与结构解析)[J]. Chinese J Magn Reson(波谱学杂志)，2009，26(1): 1 111-1 119.

[9] Ning Yong-heng(宁永成). Structural Identification of Organic Compounds and Organic Spectroscopy(有机化合物结构鉴定与有机波谱学)[M]. Beijing(北京): Science Press(科学出版社)，2000.

[10] Zou Jian-ping(邹建平)，Wang Lu(王璐)，Zeng Run-sheng(曾润生). Structural Identification of Organic Compounds(有机化合物结构分析)[M]. Beijing(北京): Science Press(科学出版社)，2005.

[11] Yu Zhen-pei(俞振培)，Yuan Jin-fang(袁晋芳)，He Xiao-ran(贺晓然)，et al. Study on the mass spectrometry of 3-ryl-4-benzoyl-l-ethoxylcarbony -1α-phenyl-1，1α，2，3，-tetrahydro-4H-azirino[1，2α][1，5]benzodiazepine[J]. J Chinese Mass Spectrom(质谱学报)， 2002，23: 141-145.

[1]	LIU Wen-qing, SONG Yan-hong, WANG Xue-lu, YAO Ye-feng. In Operando Nuclear Magnetic Resonance Spectroscopy Study on Photocatalytic Methanol Reforming [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 298-308.
[2]	YIN Tian-peng, WANG Ya-rong, WANG Min, SHI Wen-zhi, ZHANG Zheng-qian, HE Sha-sha. Complete Assignments of NMR Spectral Data of Three C₁₉-Diterpenoid Alkaloids [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 331-340.
[3]	YANG Yun-han, DU Yao, YING Fei-xiang, YANG Jun-li, XIA Da-zhen, XIA Fu-ting, YANG Li-juan. Inclusion Behavior of Naringenin/β-Cyclodextrin Supramolecular Complex [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 319-330.
[4]	HU Kun, SUN Han-dong, PUNO Pema-tenzin. Application of Quantum Chemical Calculation of Nuclear Magnetic Resonance Parameters in the Structure Elucidation of Natural Products [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 359-376.
[5]	WANG Ya-lan, WANG Xiao-jing, WANG Zhi-wei. Spectral Analyses and Structural Elucidation of Azilsartan [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 350-358.
[6]	LIU Ji-hong, JIN Kun, WANG Ping, LUO Gen. An NMR Study on Esculetin and It's Derivatives [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 341-349.
[7]	WAN Zhi-bin, SONG Jian-hui, GUO Ming-ming. The Application of in Operando Liquid State NMR on Macromolecular Material Characterization [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 408-424.
[8]	TANG Ming-xue, SCHMIDT Claudia. Estimation of Nematic Order Parameters via Haller Analysis of ¹H NMR Spectra of Liquid Crystals [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 138-147.
[9]	CAO Yuan, WU Yong-ping, CHEN Dong-jun. A Spectroscopic Study on Tautomerism of Selaginellins from Selaginella [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 155-163.
[10]	TANG Heng, Gilbert NSHOGOZA, LIU Ming-qing, LIU Ya-qian, RUAN Ke, MA Rong-sheng, GAO Jia. Identification of Novel Hits of the NSD1 SET Domain by NMR Fragment-Based Screening [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 148-154.
[11]	XIAO Xiong-jie, HU Mary, ZHANG Xu, HU Jian-zhi. An NMR-Based Metabolomics Study of Kidneys from Mice Exposed to Ionizing Radiation [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 172-181.
[12]	XU Xiao-jun, WANG Shen-lin. Probing Membrane Protein Interactions by ¹⁹F Solid-State NMR [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 238-251.
[13]	KOU Xin-hui, LIU Yi-xiang, LIU Xing-hong, LI Cong-gang, LIU Mai-li, JIANG Ling. Visualizing the Pre-Active Conformation of Response Regulator PhoB_N^F20D in Its apo State [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 164-171.
[14]	WANG Shuang-hong, ZENG Pei, PAN Si-na, WANG Jia, WANG Shu-mei, YANG Yong-xia. Effects of Gegen Qinlian Decoction on the Fecal Metabonome of High Fructose-Induced Insulin Resistance Rats Studied by ¹H NMR Spectroscopy [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 182-194.
[15]	CHEN Xiao-ying, YU Gang-jin, MAO Shi-zhen, LIU Mai-li, DU You-ru. Mixing-Induced Decreases in Critical Micelle Concentration in Aqueous Solution of Surfactants:Probing into the Mechanisms with ¹H NMR Spectroscopy [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 219-224.