Synthetic Applications of the Pyrolysis of Meldrum’s Acid Derivatives

Abd El-Aal M Gaber; Hamish McNab

doi:10.1055/s-2001-18057

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Synthesis 2001(14): 2059-2074
DOI: 10.1055/s-2001-18057

REVIEW

Synthetic Applications of the Pyrolysis of Meldrum’s Acid Derivatives

Abd El-Aal M. Gaber^a, Hamish McNab*^b
^a Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt
^b Department of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh, UK EH9 3JJ
Fax: +44(131)6504743; e-Mail: H.McNab@ed.ac.uk;

Further Information

Publication History

Received 11 July 2001
Publication Date:
09 August 2004 (online)

Abstract
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Abstract

The pyrolysis of Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione) 1 derivatives in solution and in the gas-phase takes place by loss of acetone and carbon dioxide to provide ketene intermediates. In particular, methylene Meldrum’s acid derivatives 7 often provide methyleneketenes 8, which act as substrates for internal hydrogen transfer leading to cyclisation reactions. The availability of versatile synthetic routes to 7 (in particular R = heteroatom) has led to the efficient preparation of a diverse range of cyclic compounds such as quinolinones, 3-hydroxythiophenes, naphthols, azepin-3(2H)-ones or pyrrolizin-3-ones initiated respectively by 1,3- 1,4- 1,5- 1,6- or 1,7-prototropic shifts. These reactions are discussed in the context of a rigorous understanding of the chemistry of the ketene intermediates involved. Most of the work was published in the period 1980-2000 but important references to earlier literature are also included.

1 Introduction
2 Meldrum’s Acid Derivatives
2.1 Cyclisations and Other Processes Preceded by a 1,3-Prototropic Shift
2.2 Cyclisations Preceded by a 1,4-Prototropic shift
2.3 Cyclisations Preceded by a 1,5-Prototropic Shift
2.4 Cyclisations Preceded by a 1,6-Prototropic Shift and Related Reactions
2.5 Cyclisations Preceded by a 1,7- Prototropic Shift
2.6 Cyclisations Involving Remote Prototropic Shifts
2.7 Eliminations and other Non-Cyclisation Processes
3 Coda

Key words

heterocycles - hydrogen transfer - pericyclic reactions - Meldrum’s acid - pyrolysis

References

1 McNab H. Chem. Soc. Rev. 1978, 7: 345

Crossref Google Scholar
2 Chen B.-C. Heterocycles 1991, 32: 529

Crossref Google Scholar
3 Strozhev MF. Lielbriedis IÉ. Nieland OY. Khim. Geterotsikl. Soedin. 1991, 579

Google Scholar
4 Wentrup C. Heilmayer W. Kollenz G. Synthesis 1994, 1219

Article in Thieme Connect Google Scholar
5 Kaneko C. Sato M. Sakaki J. Abe Y. J. Heterocycl. Chem. 1990, 27: 25

Crossref Google Scholar
6 Tidwell TT. Ketenes Wiley-Interscience; New York: 1995. p.125

Google Scholar
7 Brown RFC. Pyrolytic Methods in Organic Chemistry Academic Press; New York: 1980.

Google Scholar
8 Gas Phase Reactions in Organic Synthesis Vallée Y. Gordon and Breach; Amsterdam: 1997.

Google Scholar
9 McNab H. Contemp. Org. Synthesis 1996, 373

Google Scholar
11 Sato M. Ban H. Kaneko C. Tetrahedron Lett. 1997, 38: 6689

Crossref Google Scholar
12 Brown RFC. Eastwood FW. In The Chemistry of Ketenes, Allenes and Related Compounds Patai S. Wiley; Chichester: 1980. p.757

Google Scholar
13 Brown RFC. Eastwood FW. Synlett 1993, 9

Article in Thieme Connect Google Scholar
14 Brown RFC. McMullen GL. Aust. J. Chem. 1974, 27: 2385

Google Scholar
15 Wentrup C. Briehl H. LorenËak P. Vogelbacher UJ. Winter H.-W. Maquestiau A. Flammang R. J. Am. Chem. Soc. 1988, 110: 1337

Crossref Google Scholar
16a Gordon HJ. Martin JC. McNab H. J. Chem. Soc., Chem. Commun. 1983, 957

Crossref Google Scholar
16b Gordon HJ. Martin JC. McNab H. J. Chem. Soc., Perkin Trans. 1 1984, 2129

Crossref Google Scholar
17 Briehl H. Lukosch A. Wentrup C. J. Org. Chem. 1984, 49: 2772

Crossref Google Scholar
18a inventors; Sterling Drug Inc, Brit 1 147 760.
19 Ramana Rao VV. Wentrup C. J. Chem. Soc., Perkin Trans. 1 1998, 2583

Crossref Google Scholar
20 Cassis R. Tapia R. Valderrama JA. Synth. Commum. 1985, 15: 125

Crossref Google Scholar
21 For a review, see: Hermecz I. Kereszturi G. Vasvari-Debreczy L. Adv. Heterocycl. Chem. 1992, 54: 252

Google Scholar
For example:
22a Delfourne E. Roubin C. Bastide J. J. Org. Chem. 2000, 65: 5476

Crossref Google Scholar
22b Walz AJ. Sundberg RJ. J. Org. Chem. 2000, 65: 8001

Crossref Google Scholar
23 Chen B.-C. Huang X. Wang J. Synthesis 1987, 482

Article in Thieme Connect Google Scholar
24 Ye F.-C. Chen B.-C. Huang X. Synthesis 1989, 317

Article in Thieme Connect Google Scholar
25 Jeon M.-K. Kim K. Tetrahedron Lett. 2000, 41: 1943

Crossref Google Scholar
26 Bontemps N. Delfourne E. Bastide J. Francisco C. Bracher F. Tetrahedron 1997, 53: 1743

Crossref Google Scholar
27 Kitahara Y. Nakahara S. Yonezawa T. Nagatsu M. Shibano Y. Kubo A. Tetrahedron 1997, 53: 17029

Crossref Google Scholar
28 Kitahara Y. Tamura F. Nishimura M. Kubo A. Tetrahedron 1998, 54: 8421

Crossref Google Scholar
29 Derbyshire PA. Hunter GA. McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1993, 2017

Crossref Google Scholar
30 For example: Singh B. Laskowski SC. Lesher GY. Synlett 1990, 549

Article in Thieme Connect Google Scholar
31 McNab H. Withell K. Tetrahedron 1996, 52: 3163

Crossref Google Scholar
32 Yamamoto Y. Morita Y. Minami K. Chem. Pharm. Bull. 1986, 34: 1980

Google Scholar
33 Clarke D. Mares RW. McNab H. J. Chem. Soc., Perkin Trans. 1 1997, 1799

Crossref Google Scholar
34 Blake AJ. McNab H. Morrow M. Rataj H. J. Chem. Soc., Chem. Commun. 1993, 840

Crossref Google Scholar
35 McNab H. Monahan LC. In Pyrroles Part 2 Jones RA. Wiley; New York: 1992. p.525

Google Scholar
36 LorenËak P. Pommelet JC. Chuche J. Wentrup C. J. Chem. Soc., Chem. Commun. 1986, 369

Crossref Google Scholar
37 Hickson CL. Keith EM. Martin JC. McNab H. Monahan LC. Walkinshaw MD. J. Chem. Soc., Perkin Trans. 1 1986, 1465

Crossref Google Scholar
38a McNab H. Monahan LC. J. Chem. Soc., Chem. Commun. 1987, 138

Crossref Google Scholar
38b McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1988, 869

Crossref Google Scholar
39 McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1988, 863

Crossref Google Scholar
40 Blake AJ. Hunter GA. McNab H. J. Chem. Soc., Chem. Commun. 1990, 734

Crossref Google Scholar
41 Hunter GA. McNab H. J. Chem. Soc., Chem. Commun. 1993, 794

Crossref Google Scholar
42a Joucla M. Mortier J. Tetrahedron Lett. 1987, 28: 2973

Google Scholar
42b Joucla M. Mortier J. Bureau R. Tetrahedron Lett. 1987, 28: 2975

Google Scholar
42c Bureau R. Joucla M. Tetrahedron Lett. 1990, 31: 6017

Google Scholar
42d Bureau R. Mortier J. Joucla M. Tetrahedron 1992, 48: 8947

Google Scholar
42e Bureau R. Mortier J. Joucla M. Bull. Soc. Chim. Fr. 1993, 584

Google Scholar
43 Pommelet JC. Jourdain F. Dhimane H. Molecules 2000, 5: 1130

Google Scholar
44 Dhimane H. Pommelet JC. Chuche J. Lhommet G. Richaud MG. Haddad M. Tetrahedron Lett. 1985, 26: 833

Crossref Google Scholar
45 Pommelet JC. Dhimane H. Chuche J. Célérier J.-P. Haddad M. Lhommet G. J. Org. Chem. 1988, 53: 5680

Google Scholar
46 Dhimane H. Pommelet JC. Chuche J. Lhommet G. Haddad M. Tetrahedron Lett. 1987, 28: 885

Crossref Google Scholar
47 Célérier J.-P. Haddad M. Saliou C. Lhommet G. Dhimane H. Pommelet JC. Chuche J. Tetrahedron 1989, 45: 6161

Crossref Google Scholar
48 Haddad M. Célérier J.-P. Haviari G. Lhommet G. Dhimane H. Pommelet J.-C. Chuche J. Heterocycles 1990, 31: 1251

Google Scholar
49a Hunter GA. McNab H. J. Chem. Soc., Chem. Commun. 1990, 375

Crossref Google Scholar
49b Hunter GA. McNab H. J. Chem. Soc., Perkin Trans. 1 1995, 1209

Crossref Google Scholar
50 Ben Cheikh A. Dhimane H. Pommelet JC. Chuche J. Tetrahedron Lett. 1988, 29: 5919

Crossref Google Scholar
51a Chuburu F. Lacombe S. Pfister-Guillouzo G. Ben Cheik A. Chuche J. Pommelet JC. J. Am. Chem. Soc. 1991, 113: 1954

Google Scholar
51b Chuburu F. Lacombe S. Pfister-Guillouzo G. Ben Cheik A. Chuche J. Pommelet JC. J. Org. Chem. 1991, 56: 3445

Google Scholar
52 Brown RFC. Eastwood FW. Horvath JM. Aust. J. Chem. 1995, 48: 1055

Google Scholar
53 Benzies DWM. Fresneda PM. Jones RA. McNab H. J. Chem. Soc., Perkin Trans. 1 1986, 1651

Crossref Google Scholar
54 McNab H. Stobie I. J. Chem. Soc., Perkin Trans. 1 1982, 1845

Crossref Google Scholar
55 McNab H. J. Chem. Soc., Perkin Trans. 1 1983, 1203

Crossref Google Scholar
56a McNab H. Monahan LC. Gray T. J. Chem. Soc., Chem. Commun. 1987, 140

Crossref Google Scholar
56b Blake AJ. McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1989, 425

Crossref Google Scholar
57 McNab H. Monahan LC. Blake AJ. J. Chem. Soc., Perkin Trans. 1 1990, 3163

Crossref Google Scholar
58 McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1990, 3159

Crossref Google Scholar
59 McNab H. Monahan LC. J. Chem. Soc., Chem. Commun. 1987, 141

Crossref Google Scholar
60 McNab H. Monahan LC. J. Chem. Res. (S) 1990, 336

Google Scholar
61 McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1990, 3169

Crossref Google Scholar
62 Cartmell E. Mayo JE. McNab H. Sadler IH. J. Chem. Soc., Chem. Commun. 1993, 1417

Crossref Google Scholar
63 Grandjean D. Dhimane H. Pommelet JC. Chuche J. Bull. Soc. Chim. Fr. 1989, 657

Google Scholar
64 Jourdain F. Pommelet JC. Tetrahedron Lett. 1994, 35: 1545

Crossref Google Scholar
65 Jourdain F. Pommelet JC. Synth. Commun. 1997, 27: 483

Google Scholar
66 Jourdain F. Pommelet JC. Synth. Commun. 1999, 29: 1785

Google Scholar
67 McNab H. J. Org. Chem. 1981, 46: 2809

Google Scholar
68 Review: McNab H. Thornley C. Heterocycles 1994, 37: 1977

Crossref Google Scholar
69 Campbell SE. Comer MC. Derbyshire PA. Despinoy XLM. McNab H. Morrison R. Sommerville CC. Thornley C. J. Chem. Soc., Perkin Trans. 1 1997, 2195

Crossref Google Scholar
70 Blake AJ. McNab H. Morrison R. J. Chem. Soc., Perkin Trans. 1 1988, 2145

Crossref Google Scholar
71a McNab H. Thornley C. J. Chem. Soc., Chem. Commun. 1993, 1570

Crossref Google Scholar
71b McNab H. Thornley C. J. Chem. Soc., Perkin Trans. 1 2000, 3584

Crossref Google Scholar
72 Comer MC. Despinoy XLM. Gould RO. McNab H. Parsons S. Chem. Commun. 1996, 1083

Crossref Google Scholar
73 See also: McNab H. Parsons S. Stevenson E. J. Chem. Soc., Perkin Trans. 1 1999, 2047

Crossref Google Scholar
74 McNab H. J. Chem. Soc. Perkin Trans. 1 1987, 653

Crossref Google Scholar
75 McNab H. Thornley C. J. Chem. Soc., Perkin Trans. 1 1997, 2203

Crossref Google Scholar
76 Brown RFC. Coulston KJ. Eastwood FW. Manyweathers JJ. Aust. J. Chem. 1994, 47: 411

Google Scholar
77 Hunter GA. McNab H. Synthesis 1993, 1067

Article in Thieme Connect Google Scholar
78 Matsui H. Zuckerman EJ. Katagiri N. Kaneko C. Ham S. Birney DM. J. Phys. Chem. A 1997, 101: 3936

Crossref Google Scholar
79 Katagiri N. Kurimoto A. Yamada A. Sato H. Katsuhara T. Takagi K. Kaneko C. J. Chem. Soc., Chem. Commun. 1994, 281

Crossref Google Scholar
80 Katagiri N. Sato H. Kurimoto A. Okada M. Yamada A. Kaneko C. J. Org. Chem. 1994, 59: 8101

Google Scholar
81 Katagiri N. Okada M. Kaneko C. Furuya T. Tetrahedron Lett. 1996, 37: 1801

Crossref Google Scholar
82 Katagiri N. Okada M. Morishita Y. Kaneko C. Chem. Commun. 1996, 2137

Crossref Google Scholar
83 Katagiri N. Okada M. Morishita Y. Kaneko C. Tetrahedron 1997, 53: 5725

Crossref Google Scholar
84 Katagiri N. Morishita Y. Kaneko C. Heterocycles 1998, 47: 383

Google Scholar
85 Katagiri N. Morishita Y. Kaneko C. Heterocycles 1997, 46: 503

Google Scholar
86a Ham S. Birney DM. Tetrahedron Lett. 1994, 35: 8113

Crossref Google Scholar
86b Ham S. Birney DM. Tetrahedron Lett. 1997, 38: 5925

Crossref Google Scholar
87 Sato M. Yoneda N. Katagiri N. Watanabe H. Kaneko C. Synthesis 1986, 672

Article in Thieme Connect Google Scholar
88 Sato M. Sekiguchi K. Ogasawara H. Kaneko C. Synthesis 1985, 224

Article in Thieme Connect Google Scholar
89 Wentrup C. Gross G. Berstermann H.-M. LorenËak P. J. Org. Chem. 1985, 50: 2877

Google Scholar
90 Wentrup C. LorenËak P. J. Am. Chem. Soc. 1988, 110: 1880

Crossref Google Scholar
91 Bibas H. Kappe CO. Wong MW. Wentrup C. J. Chem. Soc., Perkin Trans. 2 1998, 493

Crossref Google Scholar
92 Ben Cheikh A. Chuche J. Manisse N. Pommelet JC. Netsch K.-P. LorenËak P. Wentrup C. J. Org. Chem. 1991, 56: 970

Google Scholar
93 Kappe CO. Kollenz G. Leung-Toung R. Wentrup C. J. Chem. Soc., Chem. Commun. 1992, 487

Crossref Google Scholar
94 Mosandl T. Kappe CO. Flammang R. Wentrup C. J. Chem. Soc., Chem. Commun. 1992, 1571

Crossref Google Scholar
95 Mosandl T. Stadtmüller S. Wong MW. Wentrup C. J. Phys. Chem. 1994, 98: 1080

Crossref Google Scholar
96 Fulloon BE. Wentrup C. J. Org. Chem. 1996, 61: 1363

Google Scholar
97 Wentrup C. Rao VVR. Frank W. Fulloon BE. Moloney DWJ. Mosandl T. J. Org. Chem. 1999, 64: 3608

Crossref Google Scholar
98 Moloney DWJ. Wong MW. Flammang R. Wentrup C. J. Org. Chem. 1997, 62: 4240

Crossref Google Scholar
99 Wentrup C. Kambouris P. Evans RA. Owem D. Macfarlane G. Chuche J. Pommelet JC. Ben Cheikh A. Pilsnier M. Flammang R. J. Am. Chem. Soc. 1991, 113: 3130

Crossref Google Scholar
100 Ben Cheikh A. Pommelet JC. Chuche J. J. Chem. Soc., Chem. Commun. 1990, 615

Crossref Google Scholar

10

Gaber, A. M.; McNab, H. manuscript in preparation.