Preparation of Diary Amines via Aromatization of (–)-Shikimic Acid

doi:A

Abstract

Abstract: Starting from (–)-shikimic acid, the (–)-methyl-3-dehydroshikimate could be readily obtained through esterification and IBX oxidation. The tandem reactions between primary arylamines and (–)-methyl-3-dehydroshikimate catalyzed by p-toluenesulfonic acid in CH3OH gave a series of diary amines in good yields. The present methodology was characterized by simple procedures and mild reaction conditions, representing an effective way for preparation of diary amines.

Key words: (–)-shikimic acid, (–)-methyl-3-dehydroshikimate, diary amines, aromatization

CLC Number:

O629.9

WU Wei, ZHANG En-sheng, HUANG Qi, WEI Wen, LV Ze-liang, LIU Xian-ke, YANG Shao-fan, ZOU Yong. Preparation of Diary Amines via Aromatization of (–)-Shikimic Acid[J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2012, 23(6): 722-.

References

1 Liu YY(刘永友),Liao XF(廖晓峰).Research advance in shikimic acid.Chemintimes(化工时刊),2007,21:54-57.
2 Qiu M(邱米),Ma JL(马锦林),Zhang RQ(张日清),et al.The progress in research on shikimic acid.Guangxi Forest Sci(广西林业科学),2009,38:45-47.
3 Ohira H,Torii N,Aida TM,et al.Rapid separation of shikimic acid from Chinese star anise (Illicium verum Hook. f.) with hot water extraction.Sep Purif Technol.2009,69:102-108.
4 Chou GS (仇国苏).莽草酸与禽流感治疗药-达菲.Chin J Chem Educ,2006,2:1-2.
5 Gibson JM,Thomas PS,Thomas JD,et al.Benzene-free synthesis of phenol. Angew Chem Int Ed,2001, 40: 1945-1948.
6 Kambourakis S,Frost JW.Synthesis of gallic acid:Cu2 + mediated oxidation of 3-dehydroshikimic acid.J Org Chem,2000,65:6904-6909.
7 Banwell MG,Edwards AJ,Essers M,et al.Conversion of (–)-3-dehydroshikimic acid into derivatives of the (+)-Enantiomer.J Org Chem,2003,68:6839-6841.
8 Reddy KK,Seady M,Falck JR.Intracellular mediators:Synthesis of L-α-phosphatidyl-D-myo-inositol 3,4, 5-trisphosphate and glyceryl ether analogs.J Org Chem,1995,60:3385-3390.
9 Chen Y(陈煜),Liu XK(刘现可),Wei W(魏文),et al.Syntheses and characterizations of (–)-methyl-3-dehydroshikimate and (–)-ethyl-3- dehydroshikimate.Chemistry, 2011, 74: 534-538.
10 Xue JQ(薛金强),Wang SR(王世东),Li XG(李祥高).Synthesis of diarylamine and its application in electrophotogr aphic material.Chem Ind Eng,2005,22:120-125.
11 Surry DS,Buchward S.Selective palladium-catalyzed arylation of ammonia:Synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines.J Am Chem Soc,2007,129:10354-10355.
12 Yang H,Li ZB,Shin DS,et al.A facile C–N bond formation: One-pot reaction of phenols and amines via smiles rearrangement.Synlett,2010,3:483–487.
13 Wang YF(王晔峰),Zeng JH(曾京辉),Cui XR(崔晓瑞).Recent progress in copper-catalyzed C-N coupling reactions. Chin J Org Chem,2010,30:181-199.
14 Qian Y(钱育),Wang Y(王艳),Wang LC(王龙灿),et al.Cu2O/Dimethylglyoxime catalyzed coupling reactions of aryliodides and arylamines.Chem Res Appl,2010,22:225-228.
15 Mao HF(茅海峰),Wang L(王璐),Zou JP(邹建平).A novel way to form C-N bond in LPNM media.J Suzhou Univ (Nat Sci Ed),2010,26:84-86.
16 Baltas M,Despeyroux P,Gorricbon P.Addition of amines to methyl 3-dehydroquinate and 3-dehydroshikimate.Bioorg Med Chem Lett,1993,3:1447-1452.

[1]	ZHANG Hang-qi,ZHOU Qi,FU Yan-hui,CHEN Guang-ying,YANG Na-ying. Chemical Constituents from Fissistigma retusum* [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2017, 29(2): 245-248.
[2]	XIE Lian-zhen1,2,3, XIAO Jia-qi1,2, LI Xun1,2, XIN Xue-lei1,2, AISA Hajiakber1,2. PTP1B Inhibitory Effect and Kinetics of Eremurus altaicus (Pall.) Stev.and Eremurus anisopterus (Kar.et Kir.) Regel Extract [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2017, 29(1): 1-6.
[3]	SHI Hong-yi,GAO Hai-yan,ZI Hui-min. Dyeing Properties and Component Analysis of Pigment in Green Husk of Walnut (Juglans regia* L.) [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2017, 29(1): 40-45.
[4]	XU Guo-bo1,2,LIU Jun1,XIAO Yao-hua1,ZHOU Meng1,YANG Tao2,LI Guo-you2. Isolation and Identification of Secondary Metabolites from Chaetomium globosum* CIB-160 and Their Immunological Activity [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2016, 28(10): 1562-1567.
[5]	WANG Bin1,BAI Zhi-qiang2,LIN Xiu-ping2,YANG Bin2,ZHOU Xue-feng2,LIU Yong-hong2. Chemical Constituents of an Endophytic Fungus Aspergillus flavipes* AIL8 obtained from Mangrove Acanthus ilicifolius [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2016, 28(6): 860-863.
[6]	XIE Mian-ce,LI Xian-guo,ZHANG Da-hai* . A Mini Review of OSMAC Approach and Its Application in Aspergillus fumigatus Secondary Metabolites [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2015, 27(9): 1668-1673.
[7]	WANG Jian-hong1,2*, LIAO Li-min1,2, WANG Bi1,2, LIU Teng1. Extraction of Limonin in Lemon Peel by Ultrasonic-assisted Aqueous Two-phase System [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2015, 27(6): 1081-1085.
[8]	CAO Xun,LIU Sheng,ZHOU Min,LIN Xiao-xia, WEI Wan-xing. Optimization of Aqueous Two-phase Extraction of Lignans Hypophyllanthin from Phyllanthus niruri* Using Response Surface Methodology [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2015, 27(4): 720-725.
[9]	FAN Xiao-fei 1,2, JING Lin-lin1, MA Hui-ping 1, FAN Peng-cheng1, GAO Rong-ming1,2, JIA Zheng-ping 1*. Synthesis and Anti-hypoxic Activity of Glycosyltriazole Chrysin Derivatives [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2015, 27(3): 427-431.
[10]	YANG Jin-hua,HUANG Chu-sheng*,LIU Hong-xing. Research Progress of Polymethoxyflavones with 3′,4′-Dimethoxy [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2015, 27(3): 547-551.
[11]	WANG Ying, SUN Wen, ZHANG Jing-han, XU Li-li, YANG Hong-bing. Antibacterial and Antioxidant Properties of Compounds Extracted from Petrosimonia sibirica* L. [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2015, 27(2): 251-254.
[12]	JING Lin-lin1, FAN Xiao-fei1,2, MA Hui-ping1, FAN Peng-cheng1, JIA Zheng-ping1*. Synthesis and Characterization of Glycosylated Biochanin A Derivatives [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2014, 26(12): 1916-1920.
[13]	YIN Wei*,ZHANG Guo-sheng. Study on Chemical Constituents of Rhizoma Phragmitis [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2014, 26(Suppl1): 13-15.
[14]	LUO Hong1,DAI Han-song1*,WANG Jia-wen2,WANG Tao3. A Method of Separating Camptothecin and 10-Hydroxycamptothecin from Leaves of Camptotheca Acuminate Decne in a Row [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2014, 26(Suppl2): 231-233.
[15]	ZHENG Yong-biao, PAN Hai-yue, LIU Jin, LIU Hui-juan, HUANG Jian-zhong. Chemical Constituents of the Fermented Broth and Mycelia of Hirsutella sinensis [J]. NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 2014, 26(11): 1753-1756.