Synthesis of Pyrroles in Supercritical
Carbon Dioxide: Formal [3+2] Cycloaddition
of 2-Benzoyl-Aziridines and Allenoates

Ana L. Cardoso; Rui M. D. Nunes; Luis G. Arnaut; Teresa M. V. D. Pinho e Melo

doi:10.1055/s-0030-1260209

PAPER

Synthesis of Pyrroles in Supercritical Carbon Dioxide: Formal [3+2] Cycloaddition of 2-Benzoyl-Aziridines and Allenoates

Ana L. Cardoso, Rui M. D. Nunes, Luis G. Arnaut, Teresa M. V. D. Pinho e Melo*
Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal
Fax: +351(239)827703; e-Mail: tmelo@ci.uc.pt ;

Abstract

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Abstract

The reactivity of N-benzyl- and N-cyclohexyl-2-benzoyl-3-phenylaziridines toward allenoates in supercritical carbon dioxide (scCO₂) is described. The study led to the development of a sustainable and selective approach to pyrrole derivatives and gave a new insight into the mechanism involved in the process.

Key words

cycloaddition - scCO₂ - aziridines - allenes - pyrroles

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References

For reviews, see:

<A NAME="RT68411SS-1A">1a</A> Aziridines and Epoxides in Organic Synthesis Yudin AK. Wiley-VCH Verlag; Weinheim: 2006.

<A NAME="RT68411SS-1B">1b</A> Singh GS. D’Hooghe M.
De Kimpe N. Chem. Rev. 2007, 107: 2080;

<A NAME="RT68411SS-1C">1c</A> Pearson WH. Lian BW. Bergmeier SC. In Comprehensive Heterocyclic Chemistry II Vol. 1: Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996. p.1-60

<A NAME="RT68411SS-2A">2a</A> Ungureanu I. Klotz P. Schoenfelder A. Mann A. Tetrahedron Lett. 2001, 42: 6087

<A NAME="RT68411SS-2B">2b</A> Yadav VK. Sriramurthy J. J. Am. Chem. Soc. 2005, 127: 16366

<A NAME="RT68411SS-2C">2c</A> Fan J. Gao L. Wang Z. Chem. Commun. 2009, 5021

<A NAME="RT68411SS-2D">2d</A> Wender PA. Strand D. J. Am. Chem. Soc. 2009, 131: 7528

<A NAME="RT68411SS-2E">2e</A> Gandhi S. Bisai A. Bhanu Prasad BA. Singh VK. J. Org. Chem. 2007, 72: 2133

<A NAME="RT68411SS-2F">2f</A> Krake SH. Bergmeier SC. Tetrahedron 2010, 66: 7337

<A NAME="RT68411SS-2G">2g</A> Dauban P. Malik G. Angew. Chem. Int. Ed. 2009, 48: 9026

<A NAME="RT68411SS-3">3</A> Gaebert C. Mattay J. Tetrahedron 1997, 53: 14297

<A NAME="RT68411SS-4">4</A> Zhu W. Cai G. Ma D. Org. Lett. 2005, 7: 5545

For recent examples on the ring opening of aziridinium ions by halide ions, see:

<A NAME="RT68411SS-5A">5a</A> D’Hooghe M. Catak S. Stankovic S. Waroquier M. Kim Y. Ha H.-J. Van Speybroeck V. De Kimpe N. Eur. J. Org. Chem. 2010, 4920

<A NAME="RT68411SS-5B">5b</A> Catak S. D’Hooghe M. De Kimpe N. Waroquier M.
Van Speybroeck V. J. Org. Chem. 2010, 75: 885

<A NAME="RT68411SS-6A">6a</A> Ribeiro Laia FM. Pinho e Melo TMVD. Tetrahedron Lett. 2009, 50: 6180

<A NAME="RT68411SS-6B">6b</A> Ribeiro Laia FM. Cardoso ALC. Pinho e Melo TMVD. Beja AM. Silva MR. Tetrahedron 2010, 66: 8815

For reviews on pyrrole, see:

<A NAME="RT68411SS-7A">7a</A> Sundberg RJ. In Comprehensive Heterocyclic Chemistry II Vol. 2: Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996. p.119-206

<A NAME="RT68411SS-7B">7b</A> Trofimov BA. Sobenina LN. Demenev AP. Mikhaleva AI. Chem. Rev. 2004, 104: 2481

<A NAME="RT68411SS-7C">7c</A> Fürstner A. Angew. Chem. Int. Ed. 2003, 42: 3582

<A NAME="RT68411SS-8A">8a</A> Baumgarten M. Tyutyulkov N. Chem. Eur. J. 1998, 4: 987

<A NAME="RT68411SS-8B">8b</A> Higgins SJ. Chem. Soc. Rev. 1997, 26: 247

<A NAME="RT68411SS-8C">8c</A> Anzenbacher P. Nishiyabu R. Palacios MA. Coord. Chem. Rev. 2006, 250: 2929

<A NAME="RT68411SS-8D">8d</A> Jeppesen JO. Becher J. Eur. J. Org. Chem. 2003, 3245

<A NAME="RT68411SS-9">9</A> Yamazaki S. Chem. Eur. J. 2008, 14: 6026

<A NAME="RT68411SS-10A">10a</A> Eckert CA. Knutson BL. Debenedetti PG. Nature 1996, 383: 313

<A NAME="RT68411SS-10B">10b</A> Brennecke JF. Chateauneuf JE. Chem. Rev. 1999, 99: 433

<A NAME="RT68411SS-10C">10c</A> Tucker SC. Chem. Rev. 1999, 99: 391

<A NAME="RT68411SS-10D">10d</A> Kajimoto O. Chem. Rev. 1999, 99: 355

<A NAME="RT68411SS-10E">10e</A> Munshi P. Bhaduri S. Curr. Sci. 2009, 97: 63

<A NAME="RT68411SS-11A">11a</A> Hitzler MG. Poliakoff M. Chem. Commun. 1997, 1667

<A NAME="RT68411SS-11B">11b</A> Hitzler MG. Smail FR. Ross SK. Poliakoff M. Org. Process Res. Dev. 1998, 2: 137

<A NAME="RT68411SS-11C">11c</A> King JW. Holliday RL. List GR. Snyder JM. J. Am. Oil Chem. Soc. 2001, 78: 107

<A NAME="RT68411SS-11D">11d</A> Webb PB. Sellin MF. Kunene TE. Williamson S. Slawin AMZ. Cole-Hamilton DJ. J. Am. Chem. Soc. 2003, 125: 15577

<A NAME="RT68411SS-11E">11e</A> Lu XB. Xiu JH. He R. Jin K. Luo LM. Feng XJ. Appl. Catal., A 2004, 275: 73

<A NAME="RT68411SS-11F">11f</A> Ramírez E. Recasens F. Fernández M. Larrayoz MA. AIChE J. 2004, 50: 1545

<A NAME="RT68411SS-11G">11g</A> Piqueras C. Bottini S. Damiani D. Appl. Catal., A 2006, 313: 177

<A NAME="RT68411SS-11H">11h</A> Liao W. Pan HB. Liu HW. Chen HJ. Wai CM. J. Phys. Chem. A 2009, 113: 9772

<A NAME="RT68411SS-12A">12a</A> Amandi R. Hyde JR. Ross SK. Lotz TJ. Poliakoff M. Green Chem. 2005, 7: 288

<A NAME="RT68411SS-12B">12b</A> Amandi R. Scovell K. Licence P. Lotz TJ. Poliakoff M. Green Chem. 2007, 9: 797

<A NAME="RT68411SS-13A">13a</A> Gray WK. Smail FR. Hitzler MG. Ross SK. Poliakoff M. J. Am. Chem. Soc. 1999, 121: 10711

<A NAME="RT68411SS-13B">13b</A> Licence P. Gray WK. Sokolova M. Poliakoff M.
J. Am. Chem. Soc. 2005, 127: 293

<A NAME="RT68411SS-13C">13c</A> Walsh B. Hyde JR. Licence P. Poliakoff M. Green Chem. 2005, 7: 456

<A NAME="RT68411SS-13D">13d</A> Vieville C. Mouloungui Z. Gaset A. Ind. Eng. Chem. Res. 1993, 32: 2065

<A NAME="RT68411SS-14A">14a</A> Beckman EJ. Environ. Sci. Technol. 2003, 37: 5289

<A NAME="RT68411SS-14B">14b</A> Danciu T. Beckman EJ. Hancu D. Cochran RN. Grey R. Hajnik DM. Jewson J. Angew. Chem. Int. Ed. 2003, 42: 1140

<A NAME="RT68411SS-14C">14c</A> Oakes RS. Clifford AA. Bartle KD. Pett MT. Rayner CM. Chem. Commun. 1999, 247

<A NAME="RT68411SS-15A">15a</A> Komoto I. Kobayashi S. J. Org. Chem. 2004, 69: 680

<A NAME="RT68411SS-15B">15b</A> Jacobson GB. Ted Lee C. Johnston KP. Tumas W. J. Am. Chem. Soc. 1999, 121: 11902

<A NAME="RT68411SS-15C">15c</A> Shi M. Cui SC. Li QJ. Tetrahedron 2004, 60: 6163

<A NAME="RT68411SS-16">16</A> Dunetz JR. Ciccolini RP. Fröling M. Paap SM. Allen AJ. Holmes AB. Tester JW. Danheiser RL. Chem. Commun. 2005, 4465

<A NAME="RT68411SS-17">17</A> Zetterlund PB. Aldabbagh F. Okubo M. J. Polym. Sci., Part A: Polym. Chem. 2009, 47: 3711

<A NAME="RT68411SS-18">18</A> Fürstner A. Ackermann L. Beck K. Hori H. Koch D. Langemann K. Liebl M. Six C. Leitner W. J. Am. Chem. Soc. 2001, 123: 9000

<A NAME="RT68411SS-19">19</A> Ballini R. Noè M. Perosa A. Selva M. J. Org. Chem. 2008, 73: 8520

<A NAME="RT68411SS-20">20</A> Brummond KM. Wach CK. Mini-Rev. Org. Chem. 2007, 4: 89

<A NAME="RT68411SS-21A">21a</A> Gomes PJS. Nunes CM. Pais AACC. Pinho e Melo TMVD. Arnaut LG. Tetrahedron Lett. 2006, 47: 5475

<A NAME="RT68411SS-21B">21b</A> Lee CKY. Holmes AB. Al-Duri B. Leeke GA. Santos RCD. Seville JPK. Chem. Commun. 2004, 2622

<A NAME="RT68411SS-21C">21c</A> Totoe H. McGowin AE. Turnbull K. J. Supercrit. Fluids 2000, 18: 131

<A NAME="RT68411SS-21D">21d</A> Grignard B. Calberg C. Jerome C. Detrembleur C.
J. Supercrit. Fluids 2010, 53: 151

<A NAME="RT68411SS-22">22</A> Rayner CM. Org. Process Res. Dev. 2007, 11: 121

<A NAME="RT68411SS-23">23</A> Dou X.-Y. He L.-N. Yang Z.-Z. Wang J.-L. Synlett 2010, 2159

<A NAME="RT68411SS-24A">24a</A> Pinho e Melo TMVD. Cardoso ALC. Rocha Gonsalves AM. Costa Pessoa J. Paixão JA. Beja AM. Eur. J. Org. Chem. 2004, 4830

<A NAME="RT68411SS-24B">24b</A> Lambert TH. MacMillan DCW. J. Am. Chem. Soc. 2002, 124: 13646

<A NAME="RT68411SS-25">25</A> Cromwell NH. Badson RD. Harris CE. J. Am. Chem. Soc. 1943, 65: 312