Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(11): 2435-2442
DOI: 10.1055/s-0036-1588739
DOI: 10.1055/s-0036-1588739
paper
An Efficient Synthesis of 3-Phosphorylated Benzoxaboroles via the Pudovik Reaction
Further Information
Publication History
Received: 10 December 2016
Accepted after revision: 10 February 2017
Publication Date:
14 March 2017 (online)
Dedicated to Prof. Dr. Michael Schmittel on the occasion of his 60th birthday
Abstract
A simple, fast and efficient synthesis of 3-phosphorylated benzoxaboroles using the Pudovik reaction is reported. A number of diverse 3-(dialkoxyphosphoryl)-1-hydroxy-3H-2,1-benzoxaboroles were synthesised in 70–86% yield. Interesting hydrogen bond features were observed in the crystal lattice of the 5-chlorinated 3-bis(benzyloxy)phosphoryl derivative with both inter- and intramolecular C–H···O hydrogen bonds. Additionally, linear chains of intermolecular O–H···O hydrogen bonds were observed.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588739.
- Supporting Information
Primary Data
- Primary data for this article are available online at http://www.thieme-connect.com/products/ejournals/journal/10.1055/s-00000084 and can be cited
using the following DOI: 10.4125/pd0089th.
- Primary Data
-
References
- 1 Torssell K. Ark. Kemi 1957; 10: 507-507
- 2a Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Hall DG. Wiley-VCH; Weinheim: 2011
- 2b Baker SJ, Zhang Y.-K, Akama T, Lau A, Zhou H, Hernandez V, Mao W. J. Med. Chem. 2006; 49: 4447-4447
- 2c Rock FL, Mao W, Yaremchuk A, Tukalo M, Crepin T, Zhou H, Zhang Y.-K, Hernandez V, Akama T, Baker SJ, Plattner JJ, Shapiro SA, Martinis SA, Benkovic SJ, Cusack S, Alley MR. K. Science 2007; 316: 3229-3229
- 2d Zhang J, Zhu M.-Y, Lin Y.-N, Zhou H.-C. Sci. China: Chem. 2013; 56: 1372-1372
- 2e Adamczyk-Woźniak A, Borys KM, Sportzyński A. Chem. Rev. 2015; 115: 5224-5224
- 3a Tan Y.-L, White AJ. P, Widdowson DA, Wilhelm R, Williams DJ. J. Chem. Soc., Perkin Trans. 1 2001; 3269-3269
- 3b Yamamoto Y, Ishii J, Nishiyama H, Itoh K. J. Am. Chem. Soc. 2005; 127: 9625-9625
- 3c Nicolaou KC, Li H, Boddy CN. C, Li H, Koumbis AE, Hughes R, Natarajan S, Jain NF, Ramanjulu JM, Bräse S, Solomon ME. Chem. Eur. J. 1999; 5: 2602-2602
- 3d Gunasekara DS, Gerold DJ, Aalderks NS, Chandra JS, Maanu CA, Kiprof P, Zhdankin VV, Reddy MV. R. Tetrahedron 2007; 63: 9401-9401
- 3e Adamczyk-Woźniak A, Cyrański MK, Jakubczyk M, Klimentowska P, Koll A, Kołodziejczak J, Pojmaj G, Żubrowska A, Żukowska GZ, Sporzyński A. J. Phys. Chem. A 2010; 114: 2324-2324
- 3f Wienhold F, Claes D, Graczyk K, Maison W. Synthesis 2011; 4059-4059
- 3g Ding D, Zhao Y, Meng Q, Xie D, Nare B, Chen D, Bacchi CJ, Yarlett N, Zhang Y.-K, Hernandez V, Xia Y, Freund Y, Abdulla M, Ang K.-H, Ratnam J, McKerrow JH, Jacobs RT, Zhou H, Plattner JJ. ACS Med. Chem. Lett. 2010; 1: 165-165
- 3h Zhang H, Shen S, Yang X, Sun X. Chin. J. Org. Chem. 2014; 34: 2456-2456
- 3i Adamczyk-Woźniak A, Madura I, Velders AH, Sporzyński A. Tetrahedron Lett. 2010; 51: 6181-6181
- 3j Adamczyk-Woźniak A, Borys KM, Madura ID, Michałek S, Pawełko A. Tetrahedron 2013; 69: 8936-8936
- 4a Dowlut M, Hall DG. J. Am. Chem. Soc. 2006; 128: 4226-4226
- 4b Adamczyk-Woźniak A, Borys KM, Madura ID, Pawelko A, Tomecka E, Żukowski K. New J. Chem. 2013; 37: 188-188
- 4c Schumacher S, Katterle M, Hettrich C, Paulke BR, Hall DG, Scheller FW, Gajovic-Eichelmann N. J. Mol. Recognit. 2011; 24: 953-953
- 5 Cyrański MK, Jezierska A, Klimentowska P, Panek JJ, Sporzyński A. J. Phys. Org. Chem. 2008; 21: 472-472
- 6 Xie LH, Liang J, Song J, Yin CR, Huang W. Curr. Org. Chem. 2010; 14: 2169-2169
- 7a Rajan R, Stierli D, Beaudegnies R, Renold P. WO 2016113303 A1, 2016
- 7b Stierli D, Rajan R, Beaudegnies R, Renold P, Ambacher Y. WO 201613313 A1, 2016
- 8a Engel R, Cohen JL. Synthesis of Carbon–Phosphorus Bonds . 2nd ed. CRC Press LLC; Boca Raton: 2004: 17
- 8b Tayama O, Nakano A, Iwahama T, Sakaguchi S, Ishii Y. J. Org. Chem. 2004; 69: 5494-5494
- 9 Kim K, Tsay OG, Atwood DA, Churchill DG. Chem. Rev. 2011; 111: 5345-5345
- 10a Sporzyński A, Lewandowski M, Rogowska P, Cyrański MK. Appl. Organomet. Chem. 2005; 19: 1202-1202
- 10b Adamczyk-Woźniak A, Madura I, Pawełko A, Sporzyński A, Żubrowska A, Żyła J. Cent. Eur. J. Chem. 2011; 9: 199-199
- 10c Akama T, Balko T.-W, Defauw J.-M, Plattner JJ, White W.-H, Winkle J.-R, Zhang Y.-K, Zhou Y. US 20130131017 A1, 2013
- 10d Glinka T, Higuchi R, Hecker S, Eastman B, Rodny O. WO 2012109164 A1, 2012
- 11a Abell JP, Yamamoto H. J. Am. Chem. Soc. 2008; 130: 10521-10521
- 11b Engel R. Organic Reactions . Vol. 36. Kende AS. John Wiley and Sons, Inc; New York: 1988: 176
- 11c Pudovik AN, Arbuzov BA. Zh. Obshch. Khim. 1951; 21: 382-382
- 12 Yu J.-W, Huang SK. Phosphorus, Sulfur Silicon Relat. Elem. 1997; 131: 107-107
- 13 Details of the 1H NMR dilution and variable temperature experiments are included in the Supporting Information.
- 14a Bruskov VI, Bushuev VN, Okon MS, Shulyupina NV, Poltev VI. Biopolymers 1989; 28: 589-589
- 14b Cappelli A, Giorgi G, Anzini M, Vomero S, Ristori S, Rossi C, Donati A. Chem. Eur. J. 2004; 10: 3177-3177
- 14c Donati A, Ristori S, Bonechi C, Panza L, Martini G, Rossi C. J. Am. Chem. Soc. 2002; 124: 8778-8778
- 15 Desiraju GR. Acc. Chem. Res. 1996; 29: 441-441
- 16 CCDC 1521218 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.