One-Pot Cyclizations of (2,4-Dioxobutylidene)phosphoranes
and (2-Alkoxy-4-oxobut-2-enylidene)phosphoranes

Holger Feist; Peter Langer

doi:10.1055/s-0028-1083256

REVIEW

One-Pot Cyclizations of (2,4-Dioxobutylidene)phosphoranes and (2-Alkoxy-4-oxobut-2-enylidene)phosphoranes

Holger Feist^a, Peter Langer*^a,b
^a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
^b Leibniz-Institut für Katalyse e. V. , Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Abstract

All articles of this category

Abstract

(2,4-Dioxobutylidene)phosphoranes and (2-alkoxy-4-oxobut-2-enylidene)phosphoranes are readily available and represent versatile building blocks in one-pot cyclizations. Their reactions with various electrophiles, such as 1,3-dicarbonyl compounds, enones, α-halo ketones, or hydrazine derivatives, allow a convenient synthesis of a variety of carbocyclic and heterocyclic ring systems.

1 Introduction

2 (2,4-Dioxobutylidene)phosphoranes

2.1 Synthesis

2.2 Cyclization Reactions

2.2.1 Formation of Five-Membered Carbacycles

2.2.2 Formation of Six-Membered Carbacycles

2.2.3 Formation of Seven-Membered Carbacycles

2.2.4 Formation of Heterocycles

3 (2-Alkoxy-4-oxobut-2-enylidene)phosphoranes

3.1 Synthesis

3.2 Cyclization Reactions

3.2.1 Five-Membered Rings

4 Summary

Key words

arenes - cyclizations - one-pot reactions - heterocycles - phosphoranes

Full Text

References

For reviews of Wittig reactions, see:

1a Bestmann HJ. Klein O. In Houben-Weyl Methoden der organischen Chemie Vol. 5/1b: Mueller E. Thieme; Stuttgart: 1972. p.383

1b Maryanoff BE. Reitz AB. Chem. Rev. 1989, 89: 863

1c Abell AD. Edmonds MK. Organophosphorus Reagents Murphy P. Oxford University Press; Oxford UK: 2004. p.99

1d Vedejs E. Peterson MJ. Advances in Carbanion Chemistry Vol. 2: JAI Press; New York: 1996. p.1

1e Vedejs E. Peterson MJ. Top. Stereochem. 1994, 21: 1

2a Tietze LF. Beifuss U. Angew. Chem., Int. Ed. Engl. 1993, 32: 137

2b Tietze LF. Chem. Rev. 1996, 96: 115

2c Tietze LF. Brasche G. Gericke KM. Domino Reactions in Organic Synthesis Wiley-VCH; Weinheim: 2006.

3a Patre RE. Gawas S. Sen S. Parameswaran PS. Tilve SG. Tetrahedron Lett. 2007, 48: 3517

3b Varseev GN. Maier ME. Org. Lett. 2007, 9: 1461

3c Wu J. Sun L. Dai W.-M. Tetrahedron 2006, 62: 8360

3d Jarosz S. Szewczyk K. Tetrahedron Lett. 2001, 42: 3021

3e Jarosz S. Skóra S. Tetrahedron: Asymmetry 2000, 11: 1425

3f Jarosz S. Skóra S. Tetrahedron: Asymmetry 2000, 11: 1433

3g Jarosz S. J. Chem. Soc., Perkin Trans. 1 1997, 3579

4a Herdeis C. Küpper P. Plé S. Org. Biomol. Chem. 2006, 4: 524

4b Herdeis C. Telser J. Eur. J. Org. Chem. 1999, 1407

4c Herdeis C. Schiffer T. Synthesis 1997, 1405

5a Blanco G. Quintela JM. Peinador C. Tetrahedron 2007, 63: 2034

5b Zhao J.-F. Xie C. Xu S.-Z. Ding M.-W. Xiao W.-J. Org. Biomol. Chem. 2006, 4: 130

5c Yuan J.-Z. Fu B.-Q. Ding M.-W. Yang G.-F. Eur. J. Org. Chem. 2006, 4170

5d Ding M.-W. Huang N.-Y. He H.-W. Synthesis 2005, 1601

5e Ding M.-W. Chen Y.-F. Huang N.-Y. Eur. J. Org. Chem. 2004, 3872

5f Ding M.-W. Fu B.-Q. Cheng L. Synthesis 2004, 1067

5g Wang H.-Q. Liu Z.-J. Yang L.-M. Ding M.-W. J. Heterocycl. Chem. 2004, 41: 393

5h Molina P. Fresneda PM. Delgado S. Bleda JA. Tetrahedron Lett. 2002, 43: 1005

5i Molina P. Fresneda PM. García-Zafra S. Almendros P. Tetrahedron Lett. 1994, 35: 8851

6a Mali RS. Joshi PP. Sandhu PK. Manekar-Tilve A. J. Chem. Soc., Perkin Trans. 1 2002, 371

6b Mali RS. Pandhare NA. Sindkhedkar MD. Tetrahedron Lett. 1995, 36: 7109

6c Mali RS. Joshi PP. Sandhu PK. Manekar-Tive A. J. Chem. Soc., Chem. Commun. 1994, 251

6d Mali RS. Manekar AR. Tilve SG. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1987, 26: 1

7a Kawasaki T. Shinada M. Kamimura D. Ohzono M. Ogawa A. Chem. Commun. 2006, 420

7b Quesada E. Taylor RJK. Synthesis 2005, 3193

7c Kawasaki T. Terashima R. Sakaguchi K. Sekiguchi H. Sakamoto M. Tetrahedron Lett. 1996, 37: 7525

8a Lin Y.-L. Kuo H.-S. Wang Y.-W. Huang S.-T. Tetrahedron 2003, 59: 1277

8b Zhang R.-Y. Zhao C.-G. Chem. Commun. 1996, 511

8c Kinder FR. Jarosinski MA. Anderson WK. J. Org. Chem. 1991, 56: 6475

8d Hatanaka M. Himeda Y. Ueda I. J. Chem Soc., Chem. Commun. 1990, 526

8e Baz ureau JP. Roux JL. Corre ML. Tetrahedron Lett. 1988, 29: 1921

8f Dartmann M. Flitsch W. Krebs B. Pandl K. Westfechtel A. Liebigs Ann. Chem. 1988, 695

8g Flitsch W. Wernsmann P. Tetrahedron Lett. 1981, 22: 719

9a Urbahns K. Kieck D. Göhrt A. Synthesis 1998, 1807

9b Yadav JS. Srinivas D. Tetrahedron Lett. 1997, 38: 7789

9c Wassermann HH. Shiraishi M. Coats SJ. Cook JD. Tetrahedron Lett. 1995, 36: 6785

9d Himeda Y. Hatanaka M. Ueda I. J. Chem Soc., Chem. Commun. 1995, 449

9e Himeda Y. Yamataka H. Ueda I. Hatanaka M. J. Org. Chem. 1997, 62: 6529

9f Burley I. Hewson T. Tetrahedron Lett. 1994, 35: 7099

10a Piva O. Comesse S. Eur. J. Org. Chem. 2000, 2417

10b McIntosh JM. Hayes IEE. Can. J. Chem. 1987, 65: 110

10c Minami T. Watanabe K. Hirakawa K. Chem. Lett. 1986, 2027

11a Breit B. Zahn SK. Tetrahedron 2005, 61: 6171

11b Breit B. Zahn SK. Angew. Chem., Int. Ed. Engl. 1999, 38: 969

12a Schobert R. Boeckmann RK. Pero JE. Org. Synth. 2005, 82: 140

12b Schobert R. Gordon GJ. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 27: Padwa A. Thieme; Stuttgart: 2004. p.1047

12c Schobert R. Gordon GJ. Curr. Org. Chem. 2002, 6: 1181

12d Bestmann HJ. Schmidt M. Schobert R. Synthesis 1988, 49

12e Bestmann HJ. Sandmeier D. Angew. Chem., Int. Ed. Engl. 1975, 14: 634

13a Schobert R. Wicklein A. Synthesis 2007, 1499

13b Schobert R. Dietrich M. Mullen G. Urbina-Gonzales J.-M. Synthesis 2006, 3902

13c Schobert R. Jagusch C. J. Org. Chem. 2005, 70: 6129

13d Schobert R. Jagusch C. Synthesis 2005, 2421

13e Schobert R. Stangl A. Tetrahedron Lett. 2005, 46: 1127

13f Schobert R. Jagusch C. Melanophy C. Mullen G. Org. Biomol. Chem. 2004, 2: 3524

13g Schobert R. Jagusch C. Tetrahedron Lett. 2003, 44: 6449

13h Schobert R. Siegfried S. Nieuwenhuyzen M. Milius W. Hampel F. J. Chem. Soc., Perkin Trans. 1 2000, 1723

13i Löffler J. Schobert R. Liebigs Ann./Recl. 1997, 217

13j Löffler J. Schobert R. J. Chem. Soc., Perkin Trans. 1 1996, 2799

13k Bestmann HJ. Schmid D. Sandmeier D. Schade G. Oechsner H. Chem. Ber. 1985, 118: 1709

14a Saalfrank RW. Hafner W. Markmann J. Welch A. Peters K. von Schnering HG. Z. Naturforsch. B 1994, 49: 389

14b Saalfrank RW. Schierling P. Schaetzlein P. Chem. Ber. 1983, 116: 1463

14c Saalfrank RW. Schierling P. Hafner W. Chem. Ber. 1983, 116: 3482

14d Saalfrank RW. Ackermann E. Winkler H. Paul W. Boehme R. Chem. Ber. 1980, 113: 2950

14e Bestmann HJ. Saalfrank RW. Chem. Ber. 1976, 109: 403

15 Minami T. Motoyoshiya J. Synthesis 1992, 333

16 Hatanaka M. Tanaka Y. Himeda Y. Ueda I. Tetrahedron Lett. 1993, 34: 4837

17 Reichardt C. Solvents and Solvent Effects in Organic Chemistry 2nd ed.: VCH; Weinheim: 1988.

18 Pietrusiewicz KM. Monkiewicz J. Tetrahedron Lett. 1986, 27: 739

19 Sharma GVM. Rajendra Prasad T. Radha Krishna P. Krishnudu K. Ramana Rao MHV. Kunwar AC. J. Carbohydr. Chem. 2002, 21: 501

20 Guiney D. Gibson CL. Suckling CJ. Org. Biomol. Chem. 2002, 664

21 Corey EJ. Kamiyama K. Tetrahedron Lett. 1990, 31: 3995

22 Jamie JF. Rickards RW. J. Chem. Soc., Perkin Trans. 1 1997, 3613

23 Moorhoff CM. Schneider DF. Tetrahedron Lett. 1987, 28: 4721

24 Moorhoff CM. J. Chem. Soc., Perkin Trans. 1 1997, 1987

25 Muxfeldt H. Grethe G. Uhlig K. Zeugner H. Chem. Ber. 1963, 96: 2943

26 Serratosa F. Sole E. An. R. Soc. Esp. Fis. Quim., Ser. 1966, 62: 431 ; Chem. Abstr. 1967, 66, 2623f

27 Kato N. Katagiri N. Takashima K. J. Chem. Soc., Chem. Commun. 1982, 664

28 Pietrusiewicz KM. Monkiewicz J. J. Org. Chem. 1983, 48: 788

29 Bodalski R. Pietrusiewicz KM. Monkiewicz J. Koszuk J. Tetrahedron Lett. 1980, 21: 2287

30 Davis M. Wu W.-Y. Aust. J. Chem. 1988, 41: 1591

31 Sun KM. Dawe RD. Fraser-Reid B. Carbohydr. Res. 1987, 171: 35

32 Holtz E. Albrecht U. Langer P. Tetrahedron 2007, 63: 3293

33 Lopez Herrera FJ. Uraga Baelo C. Carbohydr. Res. 1985, 139: 95

34 Hatanaka M. Tanaka Y. Ueda I. Tetrahedron Lett. 1995, 36: 3719

35 Hatanaka M. Ishida A. Tanaka Y. Himeda Y. Ueda I. Tetrahedron Lett. 1996, 37: 401

36 Karagiri N. Takashima K. Haneda T. Kato T. J. Chem. Soc., Perkin Trans. 1 1984, 553

37 Zbiral E. Oehler E. Chem. Ber. 1980, 113: 2852

38 Moorhoff CM. Monatsh. Chem. 2003, 134: 429

39 Sancaktar EA. Taylor JD. Hay JV. Wolfe JF. J. Org. Chem. 1976, 41: 509

40a Langer P. Kracke B. Synlett 2001, 1790

40b Pietrusiewicz KM. Salamoñczyk I. J. Org. Chem. 1988, 53: 2837

40c Gurjar MK. Rama Devi T. Reddy KL. Sharma PA. Murali Dhar TG. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993, 32: 995

40d Sharma GVM. Subhash Chander A. Radha Krishna P. Krishnudu K. Ramana Rao MHV. Kunwar AC. Tetrahedron: Asymmetry 2000, 11: 2643

41 Sharma GVM. Rajendra Prasad T. Radha Krishna P. Krishnudu K. Ramana Rao MHV. Kunwar AC. Tetrahedron: Asymmetry 2000, 11: 4499

42 For a detailed discussion on the analogous NaH-RONa complex, see: Caubère P. Top. Curr. Chem. 1978, 73: 105

43 Moorhoff CM. Schneider DF. Winkler D. J. Chem. Res., Miniprint 1998, 3461

44 Bankwell MG. Cameron JM. Tetrahedron Lett. 1996, 37: 525

45 Polonsky J. Varon Z. Jacquemin H. Donnelly DMX. Meegan MJ. J. Chem. Soc., Perkin Trans. 1 1980, 2065

46 Tanenbaum SW. Agarwal SC. Williams T. Pitcher RG. Tetrahedron Lett. 1970, 2377

47a Nishikawa H. Nippon Nogei Kagaku Kaishi 1933, 9: 772

47b Sasaki M. Kaneko Y. Oshita K. Takamatsu H. Yokotsuka T. Agric. Biol. Chem. 1970, 34: 1296

47c Grove JF. Pople M. J. Chem. Soc., Perkin Trans. 1 1979, 2048

48 Stodola FH. Cabot C. Benjamin C. Biochem. J. 1964, 93: 92

49 Moorhoff CM. J. Chin. Chem. Soc. 2003, 50: 419

50 Miyamoto M. Kanamatsu Y. Kawashima K. Shimohasa M. Tanaka K. Tatsuoka S. Nakanishi K. Tetrahedron 1967, 23: 421

51 Bakhaeva GP. Berlin AY. Boldyreva E. Chuprunova OA. Kolosov MN. Soifer VS. Vasiljeva TE. Yartseva IV. Tetrahedron Lett. 1968, 32: 3595

52 Berlin AY. Kieseleva OA. Shemyakin MN. Soifer VS. Yartseva IV. Kuznetsov YD. Nature 1968, 218: 193

53 Kimura Y. Mizuno T. Shimada A. Tetrahedron Lett. 1996, 37: 469

54 Kraus GA. Zheng D. Synlett 1993, 71

55 For a review on the chemistry and biology of Taxol, see: Nicolaou KC. Dai W.-M. Guy RK. Angew. Chem., Int. Ed. Engl. 1994, 33: 15

56 Hegde SG. Bryant RD. Synth. Commun. 1993, 23: 2753

57 Clerici F. Folpini E. Gelmi ML. Pocar D. Tetrahedron 1991, 47: 8907

58 Römpp Lexikon Naturstoffe Steglich W. Fugmann B. Lang-Fugmann S. Thieme; Stuttgart: 1997.

59 Pettit GR. Toki B. Herald DL. Verdier-Pinard P. Boyd MR. Hamel E. Pettit RK. J. Med. Chem. 1998, 41: 1688

60 Liou J.-P. Chang J.-Y. Chang C.-W. Chang C.-Y. Mahindroo N. Kuo F.-M. Hsieh H.-P. J. Med. Chem. 2004, 47: 2897

61 Liou J.-P. Chang C.-W. Song JS. Yang YS. Yeh CF. Tseng HY. Lo YK. Chang C.-L. Chang CM. Hsieh H.-P. J. Med. Chem. 2002, 45: 2556

62 Holtz E. Langer P. Synlett 2003, 402

63 Albrecht U. Nguyen THV. Langer P. J. Org. Chem. 2004, 69: 3417

64a Gill M. Steglich W. Prog. Chem. Org. Nat. Prod. 1987, 51: 1

64b Shi Q. Verdier-Pinard P. Brossi A. Hamel E. McPhail AT. Lee K.-H. J. Med. Chem. 1997, 40: 961

64c Shi Q. Chen K. Brossi A. Verdier-Pinard P. Hamel E. McPhail AT. Lee K.-H. Helv. Chim. Acta 1998, 81: 1023

64d Dürckheimer W. Paulus EF. Angew. Chem., Int. Ed. Engl. 1985, 24: 224 ; Angew. Chem. 1985, 97, 219

64e Klostermeyer D. Knops L. Sindlinger T. Polborn K. Steglich W. Eur. J. Org. Chem. 2000, 603

65a Friedrichsen W. In Comprehensive Heterocyclic Chemistry Vol. 2: Katritzky AR. Rees CW. Scriven EFV. Elsevier; Amsterdam: 1996. p.359 ; and references cited therein

65b König B. In Science of Synthesis Vol. 9: Maas G. Thieme; Stuttgart: 2000. p.183

65c Marshall JA. Sehon CA. J. Org. Chem. 1995, 60: 5966

65d Sperry JB. Whitehead CR. Ghiviriga I. Walczak RM. Wright DL. J. Org. Chem. 2004, 69: 3726

65e Shun ALKS. Tykwinski RR. J. Org. Chem. 2003, 68: 6810

66 Mross G. Holtz E. Langer P. J. Org. Chem. 2006, 71: 8045

67 Holtz E. Langer P. Synlett 2004, 1805

68a D’Ambrosio M. Guerriero A. Pietra F. Helv. Chim. Acta 1987, 70: 2019

68b D’Ambrosio M. Guerriero A. Pietra F. Helv. Chim. Acta 1988, 71: 964

68c Ciomei M. Albanese C. Pastori W. Grandi M. Pietra F. D’Ambrosio M. Guerriero A. Battistini C. Proc. Am. Assoc. Cancer Res. 1997, 38: Abstract 30

68d Battistini C, Ciomei M, Pietra F, D’Ambrosio M, and Guerriero A. inventors; PCT Int. Appl. WO 36335. (Pharmacia S.p.A.)

69a Lindel T. Jensen PR. Fenical W. Long BH. Casazza AM. Carboni J. Fairchild CR. J. Am. Chem. Soc. 1997, 119: 8744

69b Fenical W, Jensen PR, and Lindel T. inventors; US Patent A5473057. (University of California) ; Chem. Abstr. 1996, 124, P194297z

70 Nicolaou KC. Kim S. Pfefferkorn J. Xu J. Ohshima T. Hosokawa S. Vourloumis D. Li T. Angew. Chem., Int. Ed. Engl. 1998, 37: 1418

71a Ceccarelli SM. Piarulli U. Gennari C. Tetrahedron 2001, 57: 8531

71b Ceccarelli S. Piarulli U. Gennari C. Tetrahedron Lett. 1999, 40: 153

72 Gelmi ML. Pocar D. Synthesis 1992, 453

73 Hatanaka M. Imashiro R. Ueda I. Chem. Lett. 1992, 2253

74 Hatanaka M. Himeda Y. Imashiro R. Tanaka Y. Ueda I. J. Org. Chem. 1994, 59: 111

75 Cao W. Ding W. Yi T. Zhu Z. J. Fluorine Chem. 1997, 81: 153

76 Yang Z. Shannon D. Truong V.-L. Deslongchamps P. Org. Lett. 2002, 4: 4693

77 Kawano T. Negoro K. Ueda I. Tetrahedron Lett. 1997, 47: 8219

78 Chapdelaine D. Dube P. Deslongchamps P. Synlett 2000, 1819

79 Tanaka Y. Kawano T. Islam S. Nishioka H. Hatanaka M. Ueda I. Chem. Pharm. Bull. 1996, 44: 885

80 Bestmann H.-J. Roth K. Angew. Chem., Int. Ed. Engl. 1981, 20: 575

81 Bestmann H.-J. Saalfrank RW. Chem. Ber. 1976, 109: 403

82 Moorhoff CM. Monatsh. Chem. 2003, 134: 61

83 Himeda Y. Hiratani K. Hatanaka M. Ueda I. J. Chem. Soc., Chem. Commun. 1992, 1684

84 Hatanaka M. Himeda Y. Ueda I. Tetrahedron Lett. 1991, 35: 4521

85 Schoop A. Greiving H. Göhrt A. Tetrahedron Lett. 2000, 41: 1913

86a King ML. Chiang CC. Ling HC. Fujita E. Ochiai M. McPhail AT. J. Chem. Soc., Chem. Commun. 1982, 1150

86b Satasook C. Isman MB. Wiriyachitra P. Pestic. Sci. 1992, 36: 53

86c Janprasert J. Satasook C. Sukumalanand P. Champagne DE. Isman MB. Wiriyachitra P. Towers GH. Phytochemistry 1993, 32: 67

86d Nugroho BW. Edrada RA. Güssregen B. Wray V. Witte L. Proksch P. Phytochemistry 1997, 44: 1455

87 Takayasu T. Nitta M. J. Chem. Soc., Perkin Trans. 1 1997, 681

88 Takayasu T. Nitta M. J. Chem. Soc., Perkin Trans. 1 1997, 3255

89 Himeda Y. Tanaka Y. Ueda I. Hatanaka M. J. Chem. Soc., Perkin Trans. 1 1998, 1389

90 Hatanaka M. Himeda Y. Tanaka Y. Ueda I. Tetrahedron Lett. 1995, 36: 3211

91 Kitano H. Fujita S. Takehara Y. Hattori M. Morita T. Matsumoto K. Hatanaka M. Tetrahedron 2003, 59: 2673