Synthesis of 3,6 (8)-Disubstituted -2,4-Dihydro-1,3-benzoxazines via Mannich Reaction and Their Fungicidal Activity

doi:10.3724/SP.J.1095.2013.20507

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

Synthesis of 3,6 (8)-Disubstituted -2,4-Dihydro-1,3-benzoxazines via Mannich Reaction and Their Fungicidal Activity

TANG Zilong^1,2,3*, XIA Zanwen¹, MA Hongwei¹, LIU Hanwen^1,2,3, OU Xiaoming^2,4

(1.School of Chemistry and Chemical Engineering,Hunan University of Science and Technology，Xiangtan 411201,China;
2.Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education,
Hunan University of Science and Technology，Xiangtan 411201,China；
3.Hunan Provincial University,Key Laboratory of QSAR/QSPR Hunan University of Science and Technology,Xiangtan 411201,China;
4.National Engineering Research Center for Agrochemicals,Hunan Research Institute of Chemical Industry,Changsha 410014,China)

Received:2012-11-06 Revised:2013-01-14 Published:2013-09-10 Online:2013-09-10
Contact: Tang

Abstract

Abstract: A series of novel 3,6(8)-disubstituted 2,4-dihydro-1,3-benzoxazines was synthesized by Mannich reactions of substituted anilines with paraformaldehyde and substituted phenols in the absence of catalyst. The results show that substituted phenols and anilines with electron-donating groups on the phenyl ring give higher yields than those with electron-withdrawing groups. The structures of the products were characterized by 1H NMR, 13C NMR, IR and MS. The fungicidal activity of the title compounds was preliminarily evaluated. Compounds 4j and 4d show 86.1％ and 81.5％ activity against Sclerotonia sclerotiorum at the concentration of 25 mg/L, respectively. Compound 4i exhibits 81.6％ activity against Botrytis cinerea.

Key words: disubstituted-dihydro-benzoxazines, synthesis, Sterilization Activity

CLC Number:

O646

TANG Zilong1,2,3*, XIA Zanwen1, MA Hongwei1, LIU Hanwen1,2,3, OU Xiaoming2,4. Synthesis of 3,6 (8)-Disubstituted -2,4-Dihydro-1,3-benzoxazines via Mannich Reaction and Their Fungicidal Activity[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20507.

References

[1] Urbanski T. New Derivatives of Nitroparaffins and Their Antitubercular and Antirickettsial Properties[J]. Nature,1951,168:562-563.

[2] Kuehne M E,Konopka E A. Dihydro-1,3-oxazines as Antitumor Agents[J]. J Med Chem,1962,5(2):257-280.

[3] Kuehne M E,Konopka E A,Lambert B F. Steroidal Dihydro-1,3-oxazines as Antitumor Agents[J]. J Med Chem,1962,5(2):281-296.

[4] Bouaziz Z,Riondel J,Mey A,et al. Synthesis of Some Naphthoxazine Carbolactone Derivatives with in Vitro Cytotoxic and Antifungal Activities[J]. Eur J Med Chem,1991,26(4):469-472.

[5] Zhang P,Terefenko E A,Fensome A,et al. 6-Aryl-1,4-dihydro-benzo[d][1,3] oxazin-2-ones:a Novel Class of Potent, Selective, and Orally Active Nonsteroidal Progesterone Receptor Antagonists[J]. J Med Chem,2002,45(20):4379-4382.

[6] Wang S,Li Y,Liu Y,et al. Novel Hexacyclic Camptothecin Derivatives:Part 1.Synthesis and Cytotoxicity of Camptothecins with an a-Ring Fused 1,3-Oxazine Ring [J]. Bioorg Med Chem Lett,2008,18:4095-4097.

[7] Tang Z,Zhu Z,Xia Z,et al. Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-3-benzoxazines[J]. Molecules,2012,17:8174-8185.

[8] Tang Z,Chen W,Zhu Z,et al. Synthesis of 2,3-Diaryl-3,4-dihydro-2H-1,3-benzoxazines and Their Fungicidal Activities[J]. J Heterocycl Chem,2011,48:255-260.

[9] Kerdesky F A. A Novel and Efficient Method for the Conversion of a Trans-hexahydronaphthoxazine to a cis-Isomer Using Boron Tribromide[J]. Tetrahedron Lett,2005,46:1711-1712.

[10] Tomasulo M,Sortino S,White A,et al. Fast and Stable Photochromic Oxazines[J]. J Org Chem,2005,70:8180-8189.

[11] Deniz E,Tomasulo M,Sortino S,et al. Substituent Effects on the Photochromic of Bichromophoric Oxazines[J]. J Phys Chem C,2009,113:8491-8497.

[12] Jin L,Agag T,Yagci Y,et al. Methacryloyl-functional Benzoxazine:Photopolymerization and Thermally Activated Polymerization[J]. Macromolecules,2011,44:767-772.

[13] Baqar M,Agag T,Huang R,et al. Mechanistic Pathways for the Polymerization of Methylol-functional Enzoxazine Monomers[J]. Macromolecules,2012,45:8119-8125.

[14] Schimidt C,Straub T,Falabu D,et al. Selective Derivatisation of Resorcarenes,Mannich Reactions with Amino Alcohols[J]. Eur J Chem,2000:3937-3944.

[15] Kukharev V F,Stankevich V K,Tiumov M P,et al. A New Heterocyclic System-2,3,4,6,11b-pentahydro[1,3]-Oxazino[3,2-c][1,3]benzoxazine[J]. Chem Heterocycl Compd,2002,38(11):1434-1435.

[16] Tang Z,Chen W,Zhu Z ,et al. SnCl4-catalyzed Aza-acetalization of Aromatic Aldehydes:Synthesis of Aryl Substituted 3,4-dihydro-2H-benzoxazines[J]. Synth Commun,2012,42:1372-1383.

[17] TANG Zilong,CHANG Shuhong,YAN Lin,et al. Synthesis and Fungicidal Activity of 2-(1,3,4-Thiadiazolylaminomethyl) phenols[J]. Chinese J Appl Chem,2012,29(8):878-884(in Chinese).

唐子龙，常书红，颜林，等. 2-(1,3,4-噻二唑胺甲基)苯酚的合成及其杀菌活性[J]. 应用化学，2012,29(8):878-884.

[18] Liu A,Ou X,Huang M,et al. Synthesis and Insecticidal Activities of Novel Oxime Ether Pyrethroids[J]. Pest Manag Sci,2005,61:166-170.

[19] Mezheritskii V,Kagan E,Ardashev B. Synthesis of 2,5-Divinylpyridine by the Mannich Reaction[J]. Chem Heterocycl Compd,1967,3(4):677-678.

[20] XIAO Shangyou,ZENG Qingwen,CHEN Zhitao,et al. Mannich Reactions of Aromatic Aldehydes with Aromatic Amines and Aromatic Ketones[J]. J Chongqing Univ(Nat Sci Edn),2000,23(1):102-104,122(in Chinese).

肖尚友，曾庆文，陈志涛，等. 芳香醛与芳香酮及芳胺的曼尼希反应[J]. 重庆大学学报（自然科学版），2000,23(1):102-104,122.

Synthesis of 3,6 (8)-Disubstituted -2,4-Dihydro-1,3-benzoxazines via Mannich Reaction and Their Fungicidal Activity

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jia-Zheng LI, Shu-Zhong HE. Research Progress of Total Synthesis of Polygalolides [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 615-624.
[2]	Zhen-Bang LIU, Shuo ZHANG, Yu BAO, Ying-Ming MA, Wei-Qi LIANG, Wei WANG, Ying HE, Li NIU. Progress of Application Research on Cheminformatics in Deep Learning [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 360-373.
[3]	Yang LIU, Hai-Bao ZHANG, Qiang CHEN. Optimization of Process Parameters for Ammonia Synthesis by Nanosecond Pulsed Dielectric Barrier Discharge Plasma [J]. Chinese Journal of Applied Chemistry, 2023, 40(2): 268-276.
[4]	Rong CAO, Jie-Zhen XIA, Man-Hua LIAO, Lu-Chao ZHAO, Chen ZHAO, Qi WU. Theoretical Research Progress of Single Atom Catalysts in Electrochemical Synthesis of Ammonia [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 9-23.
[5]	Dan MENG, Kai-Yuan ZHENG, Shan-Shan CHEN, Zhao-Long ZHUO, Li-Li WANG. Preparation and Luminescence Properties of Silicon and Nitrogen Co⁃doped Carbon Dots Phosphors [J]. Chinese Journal of Applied Chemistry, 2022, 39(11): 1766-1773.
[6]	WU Zhi-Qiang, HAN Xin-Ning, LIU Yang, WANG Gang, ZHAN Hai-Juan, LIU Wan-Yi. Research Progress on Synthesis of Bis(indolyl)methanes under Aqueous or Solvent-free Catalysis [J]. Chinese Journal of Applied Chemistry, 2021, 38(8): 881-896.
[7]	BO Chun-Hui, JIANG Wei-Jia, WANG Yu-Gao, SHI Li-Hong, DONG Chuan. Research Progress on Synthesis of Coal-based Carbon Quantum Dots [J]. Chinese Journal of Applied Chemistry, 2021, 38(7): 767-788.
[8]	LIU Yang, ZHANG Hai-Bao, CHEN Qiang. Research Progress on Ammonia Synthesis Using Low Temperature Plasma [J]. Chinese Journal of Applied Chemistry, 2021, 38(6): 622-636.
[9]	LIU Yu-Ting, SUN Jia-Xi, YIN Da-Wei. Research Progress on the Synthesis and Application of Ferroncene-based Polymers [J]. Chinese Journal of Applied Chemistry, 2021, 38(4): 343-366.
[10]	XIE Zhi-Qi, ZHANG Ting, LI Ying-Wei, WANG Zhou-Jun, DAI Fei, ZHANG Rui-Rui, LIU Rui-Xia. Effect of Synthesis Conditions of Vanadium Phosphorus Oxygen (VPO) Catalyst on Catalytic Performance for Selective Oxidation of Butane [J]. Chinese Journal of Applied Chemistry, 2021, 38(4): 414-421.
[11]	GAO Feng, XU Zi-Di, GUAN Chun-Qian, WANG Yan, ZANG Yun-Hao, QU Jiang-Ying. Green Controllable Synthesis of Sulfur/Graphene Aerogel and Performance of Lithium Sulfur Battery [J]. Chinese Journal of Applied Chemistry, 2021, 38(4): 439-446.
[12]	BI Yipiao, GONG Xue, YANG Fa, RUAN Mingbo, SONG Ping, XU Weilin. Polyvalent MnO_x/C Electrocatalyst for Highly Efficient Nitrogen Reduction Reaction [J]. Chinese Journal of Applied Chemistry, 2020, 37(9): 1048-1055.
[13]	ZHANG Baohua, SHI Lanxiang. One-Pot Synthesis of Aryl/Heteroaryl Aminomethylene Bisphosphonates [J]. Chinese Journal of Applied Chemistry, 2020, 37(8): 877-882.
[14]	MENG Yating, JIAO Yuan, ZHANG Yuan, GAO Yifang, LU Wenjing, LIU Yang, DONG Chuan. Synthesis of Red Emission Fluorescent Carbon Dots and Its Application for Detection of Persulfate [J]. Chinese Journal of Applied Chemistry, 2020, 37(6): 719-725.
[15]	CHEN Lin, MIN Man, LIN Jidi. Synthesis and Antioxidation Activity of 3-Amino-7,8-dimethoxycoumarin and Its Derivatives [J]. Chinese Journal of Applied Chemistry, 2020, 37(12): 1420-1425.