三氟化硼乙醚催化合成1-(氨基甲酰基甲基)-2-烃基-3,1-苯并噁嗪类化合物

doi:10.11944/j.issn.1000-0518.2018.10.170352

摘要/Abstract

摘要：

研究了三氟化硼乙醚(BF₃·OEt₂)催化2-(N-取代氨基甲酰基甲基氨基)苯甲醇与醛的反应,发展了合成取代3,1-苯并噁嗪类化合物的方法,通过该方法合成了一系列新型结构的1-(氨基甲酰基甲基)-2-烃基-3,1-苯并噁嗪类化合物。对于这类反应BF₃·OEt₂比三甲基氯硅烷(TMSCl)和四氯化锡(SnCl₄)的普适性更广,它能有效催化这类反应,而后二者却不能。探讨了TMSCl和SnCl₄不能催化2-(N-取代氨基甲酰甲基氨基)苯甲醇与醛反应的原因。

关键词: 氮杂环化合物, 取代3,1-苯并噁嗪, 合成, BF₃·OEt₂;, 催化剂

Abstract:

Boron trifluoride diethyl etherate(BF₃·OEt₂)catalyzed reaction of 2-(N-substituted amino)benzyl alcohol with aldehyde was studied, and resulted a new method for the preparation of substituted 3,1-benzoxazine. By this method, a series of novel 1-(carbamoylmethyl)-2-aryl/alkyl-3,1-benzoxazines was prepared. It was found that BF₃·OEt₂ was a more general catalyst for these reactions than chlorotrimethylsilane and SnCl₄ for the reaction and the reason causing this difference was discussed.

Key words: nitrogen heterocycles, substituted 3,1-benzoxazines, synthesis, boron trifluoride diethyl etherate, catalyst

唐子龙,王恋,谭经照,姚园,彭丽芬. 三氟化硼乙醚催化合成1-(氨基甲酰基甲基)-2-烃基-3,1-苯并噁嗪类化合物[J]. 应用化学, 2018, 35(10): 1190-1200.

TANG Zilong,WANG Lian,TAN Jingzhao,YAO Yuan,PENG Lifeng. Boron Trifluoride Diethyl Etherate Catalyzed Synthesis of 1-(Carbamoylmethyl)-2-Aryl/Alkyl-3,1-Benzoxazines[J]. Chinese Journal of Applied Chemistry, 2018, 35(10): 1190-1200.

参考文献

[1]	Kuch H,Schmitt K,Seudl G,et al. 2-Amino-4. 2-Amino-4,4-Di-Substituted-4H-3,1-Benzoxazines:U.S.3725404[P],1973-04-03.
[2]	Sugiyama H,Hosoda K,Kumagai Y,,et al. 4H-3. 4H-3,1-Benzoxazine Derivatives, Process for Producing the Same and Agricultural or Horticultural Fungicide Containing the Same:U.S.4596801[P],1986-07-24.
[3]	Kobzina J W,Creek W. Herbicidal N-Haloacetyl-1,2-Dihydro-4H-3,1-Benzoxazine:U.S.4030906[P],1977-06-21.
[4]	Clark R D,Caroon J M,Kluge A F,et al. Synthesis and Antihypertensive Activity of 4'-Substituted Spiro[4H-3,1-Benzoxazine-4,4'-Piperidin]-3(1H)-Ones[J]. J Med Chem,1983,26(5):657-661.
[5]	Charmantray F,Demeunynck M,Carrez D,et al. 4-Hydroxymethyl-3-Aminoacridine Derivatives as a New Family of Anticancer Agents[J]. J Med Chem,2003,46(6):967-977.
[6]	Zhang P,Terefenko E A,Fensome A,et al. Potent Nonsteroidal Progesterone Receptor Agonists:Synthesis and SAR Study of 6-Aryl- Benzoxazines[J]. Bioorg Med Chem Lett,2002,12(12):787-790.
[7]	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.
[8]	Kern J C,Terefenko E A,Fensome A,et al. SAR Studies of 6-(Arylamino)-4,4-Disubstituted-1-Methyl-1,4-Dihydro-Benzo[D][1,3]-Oxazin-2-Ones as Progesterone[J]. Bioorg Med Chem Lett,2007,17(1):189-192.
[9]	Dias N,Goossens J,Baldeyrou B,et al. Oxoazabenzo[de]anthracenes Conjugated to Amino Acids:Synthesis and Evaluation as DNA-binding Antitumor Agents[J]. Bioconjugate Chem,2005,16(4):949-958.
[10]	Patel M,Ko S S,McHugh R J, et al. Synthesis and Evaluation of Analogs of Efavirenz(SustivaTM) as HIV-1 Reverse Transcriptase Inhibitors[J]. Bioorg Med Chem Lett,1999,9(19):2805-2810.
[11]	Patel M,McHugh R J,Cordova B C, et al. Synthesis and Evaluation of Benzoxazinones as HIV-1 Reverse Transcriptase Inhibitors. Analogs of Efavirenz(SustivaTM)[J]. Bioorg Med Chem Lett,1999,9(22):3221-3224.
[12]	Cocuzza A J,Chidester D R,Cordova B C,et al. Synthesis and Evaluation of Efavirenz(SustivaTM) Analogues as HIV-1 Reverse Transcriptase Inhibitors:Replacement of the Cyclopropylacetylene Side Chain[J]. Bioorg Med Chem Lett,2001,11(9):1177-1179.
[13]	Gilmore J L,Hays S J,Caprathe B W,et al. Synthesis and Evaluation of 2-Aryl-4H-3,1-Benzoxazin-4-Ones as C1r Serine Protease Inhibitors[J]. Bioorg Med Chem Lett,1996,6(6):679-682.
[14]	Hays S J,Caprathe B W,Gilmore J L,et al. 2-Amino-4H-3,1-Benzoxazi-4-Ones as C1r Serine Protease[J]. J Med Chem,1998,41(7):1060-1067.
[15]	Plummer J S,Cai C,Hays S J,et al. Benzenesulfonamide Derivatives of 2-Substituted 4H-3,1-Benzoxazin-4-Ones and Benzthiazin-4-One as Inhibitors of Complement C1r Protease[J]. Bioorg Med Chem Lett,1999,9(6):815-820.
[16]	Krantz A,Spencer R W,Tam T F,et al. Design and Synthesis of 4H-3,1-Benzoxazin-4-One as Potent Alternate Substrate Inhibitors of Human Leukocyte Elastase[J]. J Med Chem,1990,33(2):464-479.
[17]	Mizutani T,Ishikawa S,Nagase T,et al. Discovery of Novel Benzoxazinones as Potent and Orally Active Long Chain Fatty Acid Elongase 6 Inhibitors[J]. J Med Chem,2009,52(22):7289-7300.
[18]	Hanessian S,Jennequin T,Boyer N,et al. Design, Synthesis, and Optimization of Balanced Dual NK1/NK3 Receptor Antagonists[J]. ACS Med Chem Lett,2014,5(5):550-555.
[19]	Marasini B P,Rahim F,Perveen S,et al. Synthesis, Structure-Activity Relationships Studies of Benzoxazine Derivatives as α-Chymoitrypsin Inhibitor[J]. Bioorg Chem,2017,70:210-221.
[20]	Holly F W,Cope A C.Condensation Products of Aldehydes and Ketones with o-Aminobenzyl Alcohol and o-Hydroxybenzylamine[J]. J Am Chem Soc,1944,66(11):1875-1879.
[21]	Nguyen T T,Amey R L,Martin J C.Tridentate Ligand Useful in Stabilizing Coordination States of Nonmetallic Elements. An Aryldialkoxydifluoroperiodinane[J]. J Org Chem,1982,47(6):1024-1207.
[22]	Rassat A,Sieveking H U.A Stable Aromatic Diradical with Strong Dipolar Electronic Interaction[J]. Angew Chem Int Ed,1972,11(4):303-304.
[23]	Spagnol G,Rajca A,Rajca S.Efficient Synthesis of Tricyclic Benzobisoxazines by Silica Catalyst[J]. J Org Chem,2007,72(5):1867-1869.
[24]	Zhang N,Cheng R,Zhang-Negrerie D,et al. Hypervalent Iodine-Mediated Oxygenation of N,N-Diaryl Tertiary Amines:Intramolecular Functionalization of sp3 C—H Bonds Adjacent to Nitrogen[J]. J Org Chem,2014,79(21):10581-10587.
[25]	Bernárdez R,Suárez J,Fañanás-Mastral M,et al. Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Bronsted Acid Catalysis:Entry to Aromatic Oxazaheterocycles[J]. Org Lett,2016,18(4):642-645.
[26]	Tohnishi M,Nakao H,Furuya T,et al. Flubendiamide, a Novel Insecticide Highly Active Against Lepidopterous Insect Pests[J]. J Pestic Sci,2005,30(4):354-360.
[27]	Konreddy A K,Toyama M,Ito W,et al. Synthesis and Anti-Hcv Activity of 4-Hydoxyamino α-Pyranone Carboxamide Analogues[J]. ACS Med Chem Lett,2014,5(3):259-263.
[28]	Ryu J H,Lee J A,Kim S,et al. Discovery of 2-((R)-4-(2-Fluoro-4-Methylsulfonyl) Phenyl)-2-Methylpiperazin-1-Yl)-N-((1R,2S,3S,5S,7S)-5-Hydroxyadamantan-2-Yl)Pyrimidine-4-Carboxamide(SKI2852):A Highly Potent, Selective, and Orally Bioavailable Inhibitor of 11 (-hydroxysteroid Dehydrogenase Type 1(11 (-HSD1)[J]. J Med Chem,2016,59(22):10176-10189.
[29]	Robert S,Bertolla C,Masereel B,et al. Novel 3-Carboxamide-Coumarins as Potent and Selective FXIIa Inhibitors[J]. J Med Chem,2008,51(11):3077-3080.
[30]	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(2):255-260.
[31]	Tang Z,Chen W,Zhu Z,et al. SnCl4-catalyzed aza-Acetalization of Aromatic Aldehydes:Aynthesis of Aryl Substituted 3,4-Dihydro-2H-1,3-Benzoxazines[J]. Synth Commun,2012,42:1372-1383.
[32]	Narender T,Reddy K P.BF3-Et2O Mediated Biogenetic Type Synthesis of Chromanochalcones from Prenylated Chalcones via a Regioselective Cyclization Reaction[J]. Tetrahedron Lett,2007,48(43):7628-7632.
[33]	Alves M J,Azoia N G,Fortes A G.Regio- and Stereo-Delective aza-Diels-Alder Reaction of Ethyl Glyoxylate 4-Methoxyphenylimine with 1,3-Dienes in the Presence of BF3·Et2O. Evidence for a Non-Concerted Mechanism[J]. Tetrahedron,2007,63(3):727-734.
[34]	Ramos-Enríquez A M,Iglesias-Arteaga M A. Synthesis of Novel Steroids Bearing a Spirochromene Side Chain by BF3·Et2O Catalyzed Aldol Condensation of Spirostane Sapogenins and Salicylaldehyde[J]. Tetrahedron Lett,2014,55(22):3325-3327.
[35]	Wang S B,Xu X W,Fan H L,et al. Low Pressure Synthesis of Boron Nitride with (C2H5)2O·BF3 and Li3N Precursor[J]. J Cent South Univ Technol,2005,12(1):60-63.
[36]	TANG Zilong,WANG Lian,HUANG Tingting,et al. The Application and Fungicidal Activity of 1-Acyl-2-Aryl-3,1-Benzoxazines:ZL 2015103093835[P],2016-08-31(in Chinese). 唐子龙,王恋,黄婷婷,等. 具有杀菌活性的1-酰胺基-2-芳基-2,4-二氢-3,1-苯并噁嗪类化合物及其用途:中国,ZL2015103093835[P],2016-08-31.
[37]	TANG Zilong,TAN Jingzhao,CAI Lanqiong,et al. Synthesis and Fungicidal Activity of Novel 2-(Arylaminoetyl amino)Benzyl Alcohols[J]. Chinese J Appl Chem,2017,34(3):345-353(in Chinese). 唐子龙,谭经照,蔡兰琼,等. 新型2-(芳氨基乙基氨基)苯甲醇的合成及其杀菌活性[J]. 应用化学,2017,34(3):345-353.