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 2018; 50(18): 3696-3707
DOI: 10.1055/s-0037-1610195
DOI: 10.1055/s-0037-1610195
paper
Synthesis of Functionalized 1,4-Dioxanes with an Additional (Hetero)Aliphatic Ring
The work was funded by Enamine Ltd.Further Information
Publication History
Received: 04 April 2018
Accepted after revision: 30 May 2018
Publication Date:
20 July 2018 (online)
Abstract
An approach to the preparation of 2-mono-, 2,2- and 2,3-disubstituted 1,4-dioxane derivatives is described. The reaction sequence commences from readily available epoxides, in most cases prepared via the Corey–Chaikovsky reaction of the corresponding aldehydes and ketones. The key step of the method is epoxide ring opening with ethylene glycol monosodium salt, followed by further cyclization of the diols obtained. The utility of the approach was demonstrated by multigram preparation of novel functionalized 1,4-dioxanes bearing additional cycloalkane, piperidine or pyrrolidine rings, mostly spirocyclic compounds, which are advanced building blocks for medicinal chemistry.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610195.
- Supporting Information
-
References
- 1 Leeson PD. St-Gallay SA. Wenlock MC. MedChemComm 2011; 2: 91
- 2 Ritchie TJ. Macdonald SJ. F. Peace S. Pickett SD. Luscombe CN. MedChemComm 2012; 3: 1062
- 3 Lovering F. MedChemComm 2013; 4: 515
- 4 Lovering F. Bikker J. Humblet C. J. Med. Chem. 2009; 52: 6752
- 5 Vo C.-VT. Bode JW. J. Org. Chem. 2014; 79: 2809
- 6 Elliott MC. J. Chem. Soc., Perkin Trans. 1 2002; 2301
- 7 Aldeghi M. Malhotra S. Selwood DL. Chan AW. E. Chem. Biol. Drug Des. 2014; 83: 450
- 8 Kim HY. Patkar C. Warrier R. Kuhn R. Cushman M. Bioorg. Med. Chem. Lett. 2005; 15: 3207
- 9 Kim HY. Kuhn RJ. Patkar C. Warrier R. Cushman M. Bioorg. Med. Chem. 2007; 15: 2667
- 10 Katz JD. Jewell JP. Guerin DJ. Lim J. Dinsmore CJ. Deshmukh SV. Pan BS. Marshall CG. Lu W. Altman MD. Dahlberg WK. Davis L. Falcone D. Gabarda AE. Hang G. Hatch H. Holmes R. Kunii K. Lumb KJ. Lutterbach B. Mathvink R. Nazef N. Patel SB. Qu X. Reilly JF. Rickert KW. Rosenstein C. Soisson SM. Spencer KB. Szewczak AA. Walker D. Wang W. Young J. Zeng Q. J. Med. Chem. 2011; 54: 4092
- 11 Mutlib AE. Cheung HT. A. Watson TR. J. Steroid Biochem. 1987; 28: 65
- 12 Weiland J. Ritzau M. Megges R. Schön R. Watson TR. Repke KR. H. Eur. J. Med. Chem. 1995; 30: 763
- 13 McCormack WM. Finland M. Ann. Intern. Med. 1976; 84: 712
- 14 Salmon SA. Watts JL. Avian Dis. 2015; 44: 85
- 15 Pan B.-S. Chan GK. Y. Chenard M. Chi A. Davis LJ. Deshmukh SV. Gibbs JB. Gil S. Hang G. Hatch H. Jewell JP. Kariv I. Katz JD. Kunii K. Lu W. Lutterbach BA. Paweletz CP. Qu X. Reilly JF. Szewczak AA. Zeng Q. Kohl NE. Dinsmore CJ. Cancer Res. 2010; 70: 1524
- 16 Masse CE. Greenwood JR. Romero DL. Harriman GC. Wester RT. Shelley M. Kennedy-Smith JJ. Dahlgren M. Mondal S. Patent WO 2017040757, 2017
- 17 Zhang J. Zhang Y. Zhang W. Liu B. Zhang J. Liu J. Zhang L. Patent WO 2013071697, 2013
- 18 Del Bello F. Bonifazi A. Giorgioni G. Petrelli R. Quaglia W. Altomare A. Falcicchio A. Matucci R. Vistoli G. Piergentili A. Eur. J. Med. Chem. 2017; 137: 327
- 19 Del Bello F. Bonifazi A. Quaglia W. Mazzolari A. Barocelli E. Bertoni S. Matucci R. Nesi M. Piergentili A. Vistoli G. Bioorg. Med. Chem. Lett. 2014; 24: 3255
- 20 Piergentili A. Quaglia W. Giannella M. Del Bello F. Bruni B. Buccioni M. Carrieri A. Ciattini S. Bioorg. Med. Chem. 2007; 15: 886
- 21 Piergentili A. Quaglia W. Del Bello F. Giannella M. Pigini M. Barocelli E. Bertoni S. Matucci R. Nesi M. Bruni B. Di Vaira M. Bioorg. Med. Chem. 2009; 17: 8174
- 22 Yang W. Sun J. Angew. Chem. Int. Ed. 2016; 55: 1868
- 23 Li W. Waldkirch JP. Zhang X. J. Org. Chem. 2002; 67: 7618
- 24 Gu Z. Tang Y. Jiang G.-F. J. Org. Chem. 2017; 82: 5441
- 25 Wang Q. Lou J. Wu P. Wu K. Yu Z. Adv. Synth. Catal. 2017; 359: 2981
- 26 Wang J. Mou X.-Q. Zhang B.-H. Liu W.-T. Yang C. Xu L. Xu Z.-L. Wang S.-H. Tetrahedron Lett. 2016; 57: 1239
- 27 Sawant RT. Stevenson J. Odell LR. Arvidsson PI. Tetrahedron: Asymmetry 2013; 24: 134
- 28 Ghosh AK. Gemma S. Takayama J. Baldridge A. Leshchenko-Yashchuk S. Miller HB. Wang Y.-F. Kovalevsky AY. Koh Y. Weber IT. Mitsuya H. Org. Biomol. Chem. 2008; 6: 3703
- 29 Wilkinson MC. Bell R. Landon R. Nikiforov PO. Walker AJ. Synlett 2006; 2151
- 30 Stewart GW. Brands KM. J. Brewer SE. Cowden CJ. Davies AJ. Edwards JS. Gibson AW. Hamilton SE. Katz JD. Keen SP. Mullens PR. Scott JP. Wallace DJ. Wise CS. Org. Process Res. Dev. 2010; 14: 849
- 31 Schafroth MA. Rummelt SM. Sarlah D. Carreira EM. Org. Lett. 2017; 19: 3235
- 32 Astle MJ. Jacobson BE. J. Org. Chem. 1959; 24: 1766
- 33 Vishnuvajjala BR. Swain WE. Rector DH. Cook CE. Petrow V. Reel JR. Allen SK. M. Levinel SG. J. Med. Chem. 1983; 26: 426
- 34 Holmberg L. Lindberg B. Lindqvist B. Carbohydr. Res. 1995; 268: 47
- 35 Del Bello F. Barocelli E. Bertoni S. Bonifazi A. Camalli M. Campi G. Giannella M. Matucci R. Nesi M. Pigini M. Quaglia W. Piergentili A. J. Med. Chem. 2012; 55: 1783
- 36 Gu Q. You SL. Org. Lett. 2011; 13: 5192
- 37 Košiová I. Šimák O. Panova N. Buděšínský M. Petrová M. Rejman D. Liboska R. Páv O. Rosenberg I. Eur. J. Med. Chem. 2014; 74: 145
- 38 Tietze LF. Heins A. Soleiman-Beigi M. Raith C. Heterocycles 2009; 77: 1123
- 39 Tiecco M. Testaferri L. Marini F. Sternativo S. Santi C. Bagnoli L. Temperini A. Tetrahedron: Asymmetry 2003; 14: 1095
- 40 von Richter V. Ber. Dtsch. Chem. Ges. 1877; 10: 679
- 41 von Richter V. Hofferichter P. J. Prakt. Chem. 1879; 20: 188
- 42 Kohler EP. Tishler M. Potter H. Thompson HT. J. Am. Chem. Soc. 1939; 61: 1057
- 43 Zhang JQ. Luo YJ. Xiong YS. Yu Y. Tu ZC. Long ZJ. Lai XJ. Chen HX. Luo Y. Weng J. Lu G. J. Med. Chem. 2016; 59: 7268
- 44 Vermote A. Brackman G. Risseeuw MD. P. Coenye T. Van Calenbergh S. Eur. J. Med. Chem. 2017; 127: 757
- 45 Veliev MG. Shatirova MI. Askerov OV. Chem. Heterocycl. Compd. 2009; 45: 1190
- 46 Hachiya I. Matsumoto T. Inagaki T. Takahashi A. Shimizu M. Heterocycles 2010; 82: 449
- 47 Hiessböck R. Kratzel M. J. Heterocycl. Chem. 1999; 36: 1295
- 48 Kotha S. Ravikumar O. Sreevani G. Tetrahedron 2016; 72: 6611
- 49 Fedorov BS. Golovina NI. Smirnov SP. Firkin AI. Atovmyan LO. J. Chem. Res. 2002; 38: 450
- 50 Andrews CW. Rodebaugh R. Fraser-Reid B. J. Org. Chem. 1996; 61: 5280
- 51 Bagnoli L. Scarponi C. Rossi MG. Testaferri L. Tiecco M. Chem. Eur. J. 2011; 17: 993
- 52 Derzhinskii AR. Kalugin VE. Konyushkin LD. Prilezhaeva EN. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1983; 32: 641
- 53 Yu Q. Carlsen P. Molecules 2008; 13: 2962
- 54 Potapov VA. Kurkutov EO. Musalov MV. Amosova SV. Russ. J. Org. Chem. 2016; 52: 1719
- 55 Tarselli MA. Zuccarello JL. Lee SJ. Gagné MR. Org. Lett. 2009; 11: 3490
- 56 Muthusamy S. Krishnamurthi J. Suresh E. Chem. Commun. 2007; 861
- 57 Brogan JB. Zercher CK. Bauer GB. Rogers RD. J. Org. Chem. 1997; 62: 3902
- 58 Oku A. Murai N. Baird J. J. Org. Chem. 1997; 62: 2123
- 59 Duclos RI. Makriyannis A. J. Org. Chem. 1992; 57: 6156
- 60 Gadekar PK. Roychowdhury A. Kharkar PS. Khedkar VM. Arkile M. Manek H. Sarkar D. Sharma R. Vijayakumar V. Sarveswari S. Eur. J. Med. Chem. 2016; 122: 475
- 61 Balsamo A. Giorgi I. Lapucci A. Lucacchini A. Macchia B. Macchia F. Martini C. Rossi A. J. Med. Chem. 1987; 30: 222
- 62 Weng Z. Wei W. Dong X. Hu Y. Huang S. Liu T. Xie X. Monatsh. Chem. 2012; 143: 303
- 63 Someya H. Kondoh A. Sato A. Ohmiya H. Yorimitsu H. Oshima K. Synlett 2006; 3061
- 64 Soukri M. Lazar S. Pujol MD. Akssira M. Leger JM. Jarry C. Guillaumet G. Tetrahedron 2003; 59: 3665
- 65 Lightner DA. Gurst JE. Organic Conformational Analysis and Stereochemistry from Circular Dichroism Spectroscopy. Wiley-VCH; Weinheim: 2000
- 66 Dang Z. Yang Y. Ji R. Zhang S. Bioorg. Med. Chem. Lett. 2007; 17: 4523
- 67 Keeling SP. Campbell IB. Coe DM. Cooper TW. J. Hardy GW. Jack TI. Jones HT. Needham D. Shipley TJ. Skone PA. Sutton PW. Weingarten GA. Macdonald SJ. F. Tetrahedron Lett. 2008; 49: 5101
- 68 Winkler F. K. Dunits J. D. Acta Cryst. Sect. B 1975; B31: 270
- 69 Ciaccio JA. Drahus AL. Meis RM. Tingle CT. Smrtka M. Geneste R. Synth. Commun. 2003; 33: 2135