Synthesis 2015; 47(18): 2781-2790
DOI: 10.1055/s-0034-1378717
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Reactivity of Aziridines with Internal Dipolarophiles: An Approach to 1,4-Dihydrochromeno[4,3-b]pyrroles and 3-Methylenechromano[4,3-b]pyrroles

Fernanda M. Ribeiro Laia
Centro de Química de Coimbra, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal   eMail: tmelo@ci.uc.pt
,
Teresa M. V. D. Pinho e Melo*
Centro de Química de Coimbra, Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal   eMail: tmelo@ci.uc.pt
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 09. April 2015

Accepted after revision: 01. Mai 2015

Publikationsdatum:
24. Juni 2015 (online)


Abstract

Aziridines derived from 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)chalcones and from benzyl 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)phenylacrylates were prepared in a stereoselective fashion. Their reactivity as azomethine ylide precursors was examined, leading to the synthesis of 1,4-dihydrochromeno[4,3-b]pyrrole and 3-methylenechromano[4,3-b]pyrrole derivatives through intramolecular 1,3-dipolar cycloaddition reactions.

Supporting Information

 
  • References


    • For reviews, see:
    • 1a Ferreira SB, da Silva F.deC, Pinto AC, Gonzaga DT. G, Ferreira VF. J. Heterocycl. Chem. 2009; 46: 1080
    • 1b Lee T, Gong Y.-D. Molecules 2012; 17: 5467
    • 1c Patil SA, Patil R, Pfeffer LM, Miller DD. Future Med. Chem. 2013; 5: 1647
    • 1d Thomas N, Zachariah SM. Asian J. Pharm. Clin. Res. 2013; 6 (Suppl. 2) (Suppl. 02) 11
    • 1e Nicolaou KC, Pfefferkorn JA, Roecker AJ, Cao GQ, Barluenga S, Mitchell HJ. J. Am. Chem. Soc. 2000; 122: 9939

      For examples of anticancer activities, see:
    • 2a Yin S.-Q, Shi M, Kong T.-T, Zhang C.-M, Han K, Cao B, Zhang Z, Du X, Tang L.-Q, Mao X, Liu Z.-P. Bioorg. Med. Chem. Lett. 2013; 23: 3314
    • 2b Reddy KR, Rao PS, Dev GJ, Poornachandra Y, Kumar CG, Narsaiah B. Bioorg. Med. Chem. Lett. 2014; 24: 1661
    • 2c Rahmani-Nezhad S, Safavi M, Pordeli M, Ardestani SK, Khosravani L, Pourshojaei Y, Mahdavi M, Emami S, Foroumadi A, Shafiee A. Eur. J. Med. Chem. 2014; 86: 562
    • 2d Parthiban A, Kumaravel M, Muthukumaran J, Rukkumani R, Krishna R, Rao HS. P. Med. Chem. Res. 2015; 24: 1226
    • 2e Barlaam B, Cosulich S, Degorce S, Fitzek M, Green S, Hancox U, Lambert-van der Brempt C, Lohmann J.-J, Maudet M, Morgentin R, Pasquet M.-J, Péru A, Plé P, Saleh T, Vautier M, Walker M, Ward L, Warin N. J. Med. Chem. 2015; 58: 943

      For examples of other pharmacological activities, see:
    • 3a Torregroza I, Evans T, Das BC. Chem. Biol. Drug Des. 2009; 73: 339
    • 3b Chaudhari SS, Kadam AB, Khairatkar-Joshi N, Mukhopadhyay I, Karnik PV, Raghuram A, Rao SS, Vaiyapuri TS, Wale DP, Bhosale VM, Gudi GS, Sangana RR, Thomas A. Bioorg. Med. Chem. 2013; 21: 6542
    • 3c Funke M, Thimm D, Schiedel AC, Müller CE. J. Med. Chem. 2013; 56: 5182
    • 3d Harel D, Schepmann D, Prinz H, Brun R, Schmidt TJ, Wünsch B. J. Med. Chem. 2013; 56: 7442
    • 3e Pan Z.-X, He X, Chen Y.-Y, Tang W.-J, Shi J.-B, Tang Y.-L, Song B.-A, Li J, Liu X.-H. Eur. J. Med. Chem. 2014; 80: 278
    • 3f Ashok D, Lakshmi BV, Ganesh A, Ravi S, Adam S, Murthy SD. S. Russ. J. Gen. Chem. 2014; 84: 2234
  • 4 Laia FM. R, Gomes CS. B, Pinho e Melo TM. V. D. Tetrahedron 2013; 69: 10081
  • 5 Laia FM. R, Soares MI. L, Gomes CS. B, Pinho e Melo TM. V. D. Eur. J. Org. Chem. 2015; 1341
    • 6a Laia FM. R, Pinho e Melo TM. V. D. Tetrahedron Lett. 2009; 50: 6180
    • 6b Laia FM. R, Cardoso AL, Beja AM, Silva MR, Pinho e Melo TM. V. D. Tetrahedron 2010; 66: 8815
    • 6c Cardoso AL, Nunes RM. D, Arnaut LG, Pinho e Melo TM. V. D. Synthesis 2011; 3516
    • 7a Padwa A, Ku H. J. Org. Chem. 1979; 44: 255
    • 7b DeShong P, Kell DA, Sidler DR. J. Org. Chem. 1985; 50: 2309
    • 7c Takano S, Iwabuchi Y, Ogasawara K. J. Am. Chem. Soc. 1987; 109: 5523
    • 7d Takano S, Iwabuchi Y, Ogasawara K. J. Chem. Soc., Chem. Commun. 1988; 1204
    • 7e Takano S, Samizu K, Ogasawara K. Chem. Lett. 1990; 1239
    • 7f Henke BR, Kouklis AJ, Heathcock CH. J. Org. Chem. 1992; 57: 7056
    • 7g Pankova AS, Voronin VV, Kuznetsov MA. Tetrahedron Lett. 2009; 50: 5990
    • 7h Kuznetsov MA, Pankova AS, Voronin VV, Vlasenko NA. Chem. Heterocycl. Comp. 2012; 47: 1353
  • 8 Padwa A, Eisenhardt W. J. Am. Chem. Soc. 1971; 93: 1400
  • 9 Searles S, Li Y, Nassim B, Lopes M.-TR, Tran PT, Crabbé P. J. Chem. Soc., Perkin Trans. 1 1984; 747
  • 10 For the general procedure, see: Cromwell NH, Babson RD, Harris CE. J. Am. Chem. Soc. 1943; 65: 312
  • 11 Giese B, Schoch J, Rüchardt C. Chem. Ber. 1978; 111: 1395