Methylene Meldrum’s
Acid Derivatives of Indoxyl and Their Cyclization Reactions
under Flash Vacuum Pyrolysis Conditions

Alexander P. Gaywood; Hamish McNab

doi:10.1055/s-0029-1218668

PAPER

Methylene Meldrum’s Acid Derivatives of Indoxyl and Their Cyclization Reactions under Flash Vacuum Pyrolysis Conditions

Alexander P. Gaywood, Hamish McNab*
School of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, UK
Fax: +44(131)6504743; e-Mail: H.McNab@ed.ac.uk;

Abstract

Alle Artikel dieser Rubrik

Abstract

Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2′-azidoacetophenone at 650 ˚C. Reaction of indoxyl with methoxymethylene Meldrum’s acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2-methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%).

Key words

gas-phase reactions - cyclisations - heterocycles - pyrolysis - ketenes

Volltext

Referenzen

References

1 Ryabova SY. Alekseeva LM. Granik VG. Chem. Heterocycl. Cpd. (Engl. Transl.) 1991, 960

2 Derbyshire PA. Hunter GA. McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1993, 2017

Reviews:

3a Ryabova SY. Granik VG. Pharm. Chem. J. (Engl. Transl.) 1995, 29: 809

3b Merour J.-Y. Piroelle S. Joseph B. Trends Heterocycl. Chem. 1997, 5: 115

4 For example: Capon B. Kwok FC. J. Am. Chem. Soc. 1989, 111: 5346

5 Gaywood AP. McNab H. J. Org. Chem. 2009, 74: 4278

6 Review: Smalley RK. Adv. Heterocycl. Chem. 1981, 29: 1

7a Bamberger E. Elger F. Ber. Dtsch. Chem. Ges. 1903, 36: 1611

7b Azadi-Ardakani M. Alkhader MA. Lippiatt JH. Patel DI. Smalley RK. Higson S. J. Chem. Soc., Perkin Trans. 1 1986, 1107

8 Dyall LK. In The Chemistry of Halides, Pseudo-halides and Azides Supplement D, Part 1: Patai S. Rappoport Z. Wiley; Chichester: 1983. p.287

9 McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 1 1988. p.863

Reviews:

10a McNab H. Monahan LC. 3-Hydroxypyrroles, In The Chemistry of Heterocyclic Compounds Vol. 48, Part 2: Jones RA. Wiley; New York: 1992. p.525

10b Gaber AM. McNab H. Synthesis 2001, 2059

10c McNab H. Aldrichimica Acta 2004, 37: 19

11a Lukes R. Zobacova A. Chimia 1959, 13: 333

11b Laschtuvka E. Huisgen R. Chem. Ber. 1960, 93: 81

11c Huisgen R. Laschtuvka E. Chem. Ber. 1960, 93: 65

11d Merour J.-Y. Chichereau L. Desarbre E. Gadonneix P. Synthesis 1996, 519

12 McNab H. Monahan LC. J. Chem. Soc., Perkin Trans. 2 1988, 1459

13 Campo M. Larock R. J. Org. Chem. 2002, 67: 5616

14 For example: Gaywood AP. Hill L. Imam SH. McNab H. Neumajer G. O’Neill WJ. Mátyus P. New J. Chem. 2010, in press; DOI: 10.1039/b9nj00474b

15 Ryabova SY. Trofimkin YI. Alekseeva LM. Bogdanova GA. Sheinker YN. Granik VG. Chem. Heterocycl. Cpds. (Engl. Transl.) 1990, 1238

16a Tominaga Y. Natsuki R. Matsuda Y. Kobayashi G. Chem. Pharm. Bull. Jpn. 1973, 21: 1658

16b Kobayashi G. Matsuda Y. Natsuki R. Tominaga Y. Okamura T. Itamura A. Yakugaku Zasshi 1973, 93: 964

16c Tominaga Y. Natsuki R. Matsuda Y. Kobayashi G. Yakugaku Zasshi 1973, 93: 1523

16d Frew AJ. Proctor GR. Silverton JV. J. Chem. Soc., Perkin Trans. 1 1980, 1251

16e Goerlitzer K. Dehne A. Arch. Pharm. (Weinheim, Ger.) 1984, 317: 443

16f Unangst PC. Brown RE. J. Heterocycl. Chem. 1984, 21: 283

17 Dyall LK. Holmes A. Aust. J. Chem. 1988, 41: 1677

18 Hendrickson JB. Hussoin MS. J. Org. Chem. 1989, 54: 1144

19 Barth A. Corrie JET. Gradwell MJ. Maeda Y. Mäntele W. Meier T. Trentham DR. J. Am. Chem. Soc. 1997, 119: 4149

20 Dyall LK. Kemp JE. J. Chem. Soc., B 1968, 976