Tandem Hydroformylation–Biginelli Reaction

Daniela Fuchs; Mahboobeh Nasr-Esfahani; Lisa Diab; Tomáš Šmejkal; Bernhard Breit

doi:10.1055/s-0033-1339298

Synlett, Table of Contents

Synlett 2013; 24(13): 1657-1662
DOI: 10.1055/s-0033-1339298

letter

Tandem Hydroformylation–Biginelli Reaction

Daniela Fuchs

^aInstitut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Bg., Germany Fax: +49(761)2038715 Email: bernhard.breit@chemie.uni-freiburg.de

,

Mahboobeh Nasr-Esfahani

^aInstitut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Bg., Germany Fax: +49(761)2038715 Email: bernhard.breit@chemie.uni-freiburg.de

,

Lisa Diab

^aInstitut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Bg., Germany Fax: +49(761)2038715 Email: bernhard.breit@chemie.uni-freiburg.de

,

Tomáš Šmejkal

^bSyngenta Crop Protection AG, Schaffhauserstrasse, 4332 Stein, Switzerland

,

Bernhard Breit*

^aInstitut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Bg., Germany Fax: +49(761)2038715 Email: bernhard.breit@chemie.uni-freiburg.de

› Author Affiliations

Abstract

All articles of this category

Abstract

The combination of a tandem process with a multicomponent reaction is a new approach to high atom-economic synthesis. A tandem hydroformylation–Biginelli reaction sequence has been developed leading to a variety of functionalized 4-alkyl-substituted 3,4-dihydropyrimidin-2(1H)-ones.

Key words

hydroformylation - Biginelli reaction - tandem reaction - multicomponent reaction - rhodium

Full Text

References

References and Notes
1 Kappe CO. Eur. J. Med. Chem. 2000; 1043
2 Atwal K, Rovnyak GC, Schwartz J, Moreland S, Hedberg A, Gougoutas JZ, Malley MF, Floyd DM. J. Med. Chem. 1990; 33: 1510
3 Rovnyak GC, Kimball SD, Beyer B, Cucinotta G, DiMarco JD, Gougoutas J, Heldberg A, Malley M, McCarthy JP, Zhang R, Moreland SJ. J. Med. Chem. 1995; 38: 119
4 Barrow JC, Nantermet PG, Selnick HG, Glass KL, Rittle KE, Gilbert KF, Steele TG, Homnick CF, Freidinger RM, Ransom RW, Kling P, Reiss D, Broten TP, Schorn TW, Chang RS. L, O’Malley SS, Olah TV, Ellis JD, Barrish A, Kassahun K, Leppert P, Nagarathnam D, Forray C. J. Med. Chem. 2000; 43: 2703

5a daSilva DL, Resi FS, Muniz DR, Ruiz A.-LT. G, Carvalho JE, Sabino AA, Modolo LV, de Fátima A. Bioorg. Med. Chem. 2012; 20: 2645
5b For a review, see: Sandhu JS. ARKIVOC 2012; (i): 66

6a Biginelli P. Ber. Dtsch. Chem. Ges. 1891; 24: 1317
6b Biginelli P. Gazz. Chim. Ital. 1893; 23: 360
6c Kappe CO, Stadler A. Org. React. 2004; 1

7 Saha S, Moorthy JN. J. Org. Chem. 2011; 76: 396
8 Rahman M, Majee A, Hajra A. J. Heterocycl. Chem. 2010; 47: 1230
9 Stadler A, Kappe CO. J. Comb. Chem. 2001; 3: 624
10 Burns NZ, Baran PS, Hoffmann RW. Angew. Chem. Int. Ed. 2009; 48: 2854 ; Angew Chem. 2009, 121, 2896

11a Trost BM. Angew. Chem., Int. Ed. Engl. 1995; 34: 259 ; Angew. Chem. 1995, 107, 285
11b Trost BM. Science 1991; 254: 1471

12a Breit B. Top. Curr. Chem. 2007; 279: 139
12b Breit B, Seiche W. Synthesis 2001; 1
12c van Leuween PW. N. M, Claver C. Rhodium Catalyzed Hydroformylation . Springer; Berlin: 2008

13a Eilbracht P, Bärfacker L, Buss C, Hollmann C, Kitsos-Rzychon BE, Kranemann CL, Rische T, Roggenbuck R, Schmidt A. Chem. Rev. 1999; 99: 3329
13b Breit B, Zahn SK. Angew. Chem. Int. Ed. 1999; 38: 969 ; Angew. Chem. 1999, 111, 1022
13c Zahn SK, Breit B. Angew. Chem. Int. Ed. 2001; 40: 1910 ; Angew. Chem. 2001, 113, 1964
13d Abillard O, Breit B. Adv. Synth. Catal. 2007; 349: 1891
13e Köhling P, Schmidt AM, Eilbracht P. Org Lett. 2003; 5: 3213
13f Chercheja S, Nadakudity SK, Eilbracht P. Adv. Synth. Catal. 2010; 352: 637
13g Chercheja S, Rothenbücher T, Eilbracht P. Adv. Synth. Catal. 2009; 351: 339
13h Stiller J, Vorholt AJ, Ostrowski KA, Behr A, Christmann M. Chem. Eur. J. 2012; 18: 9496
13i Takahashi K, Yamashita M, Ichihara T, Nakano K, Nozaki K. Angew. Chem. Int. Ed. 2010; 49: 4488 ; Angew. Chem. 2010, 122, 4590

14 Fuchs D, Rousseau G, Diab L, Gellrich U, Breit B. Angew. Chem. Int. Ed. 2012; 51: 2178 ; Angew. Chem. 2012, 124, 2220
15 Kranenburg M, van der Burgt YE. M, Kamer PC. J, van Leeuwen PW. N. M, Goubitz K, Fraanje J. Organometallics 1995; 14: 3081
16 Details about effects of different solvents and concentrations can be found in the Supporting Information.
17 Palucki M, Hughes DL, Yang C, Yasuda N. US 6262268 B1, 2001
18 Brown HC, Lynch GJ. J. Org. Chem. 1981; 46: 531
19 Rawat V, Chouthaiwale PV, Suryavanshi G, Sudalai A. Tetrahedron: Asymmetry 2009; 20: 2173
20 Breit B, Seiche W. J. Am. Chem. Soc. 2003; 125: 6608
21 Schleicher KD, Jamison TF. Org. Lett. 2007; 9: 875
22 Kemme ST, Smejkal T, Breit B. Adv. Synth. Catal. 2008; 350: 989
23 Cravotto G. WO 2003/106397 A1, 2003

Supplementary Material

Supporting Information