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Synthesis 2014; 46(10): 1362-1366
DOI: 10.1055/s-0033-1341102
DOI: 10.1055/s-0033-1341102
special topic
A Facile Route to H-Pyrazolo[5,1-a]isoquinolines through a Multicomponent Reaction of 2-Alkynylbenzaldehyde, Sulfonylhydrazine, and Benzyne
Weitere Informationen
Publikationsverlauf
Received: 09. Februar 2014
Accepted after revision: 13. März 2014
Publikationsdatum:
28. März 2014 (online)

Abstract
A facile and efficient route for the generation of H-pyrazolo[5,1-a]isoquinolines via a silver triflate catalyzed three-component reaction of 2-alkynylbenzaldehyde, tosylhydrazine, and benzyne is reported. This reaction proceeds smoothly under mild conditions with high efficiency.
Key words
2-alkynylbenzaldehyde - benzyne - H-pyrazolo[5,1-a]isoquinoline - silver triflate - tosylhydrazineSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are experimental procedure, characterization data, and 1H and 13C NMR spectra of compounds 3.
- Supporting Information
-
References and Notes
- 1a Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals . 2nd ed., Vols. 1 and 2; Beller M, Bolm C. Wiley-VCH; Weinheim: 2004
- 1b D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
- 1c Díez-González S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612
- 1d Das S, Brudvig GW, Crabtree RH. Chem. Commun. 2008; 413
- 2a Enantioselective Organocatalysis: Reactions and Experimental Procedures. Dalko PI. Wiley-VCH; Weinheim: 2007
- 2b Seayad J, List B. Org. Biomol. Chem. 2005; 3: 719
- 2c MacMillan DW. C. Nature (London) 2008; 455: 304
- 2d Berkessel A, Gröger H In Asymmetric Organocatalysis: From Biomimetic Concepts to Application in Asymmetric Synthesis. Wiley-VCH; Weinheim: 2005
- 2e Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138
- 2f Gaunt MJ, Johansson CC. C, McNally A, Vo NT. Drug Discovery Today 2007; 12: 8
- 2g Pellissier H. Tetrahedron 2007; 63: 9267
- 2h Dondoni A, Massi A. Angew. Chem. Int. Ed. 2008; 47: 4638
- 3a Walsh DP, Chang Y.-T. Chem. Rev. 2006; 106: 2476
- 3b Arya P, Chou DT. H, Baek M.-G. Angew. Chem. Int. Ed. 2001; 40: 339
- 3c Schreiber SL. Science (Washington, D.C.) 2000; 287: 1964
- 3d Burke MD, Schreiber SL. Angew. Chem. Int. Ed. 2004; 43: 46
- 3e Schreiber SL. Nature (London) 2009; 457: 153
- 3f Tan DS. Nat. Chem. Biol. 2005; 1: 74
- 3g Cordier C, Morton D, Murrison S, Nelson A, O’Leary-Steele C. Nat. Prod. Rep. 2008; 25: 719
- 4a Terrett NK. Combinatorial Chemistry . Oxford University Press; New York: 1998
- 4b Zhu J, Bienaymé H. Multicomponent Reactions . Wiley-VCH; Weinheim: 2005
- 4c Toure BB, Hall DG. Chem. Rev. 2009; 109: 4439
- 4d Candeias NR, Montalbano F, Cal PM. S. D, Gois PM. P. Chem. Rev. 2010; 110: 6169
- 5 Selected example, see: Balamurugan K, Perumal S, Menéndez JC. Tetrahedron 2011; 67: 3201 ; and references therein
- 6 Chen Z, Wu J. Org. Lett. 2010; 12: 4856
- 7a Li S, Wu J. Org. Lett. 2011; 13: 712
- 7b Ye S, Yang X, Wu J. Chem. Commun. 2010; 46: 5238
- 7c Yu X, Ye S, Wu J. Adv. Synth. Catal. 2010; 352: 2050
- 7d Yu X, Chen Z, Yang X, Wu J. J. Comb. Chem. 2010; 12: 374
- 7e Chen Z, Gao L, Ye S, Ding Q, Wu J. Chem. Commun. 2012; 48: 3975
- 7f Li S, Luo Y, Wu J. Org. Lett. 2011; 13: 4312
- 7g Liu G, Liu H, Qiu G, Pu S, Wu J. Chem. Commun. 2012; 48: 7049
- 8a Zhao J, Li P, Wu C, Chen H, Ai W, Sun R, Ren H, Larock RC, Shi F. Org. Biomol. Chem. 2012; 10: 1922
- 8b Jiang L, Yu X, Fang B, Wu J. Org. Biomol. Chem. 2012; 10: 8102
- 9 Pan X, Luo Y, Wu J. J. Org. Chem. 2013; 78: 5756
- 10a Kessar SV In Comprehensive Organic Synthesis . Vol. 4. Trost BM, Fleming I. Pergamon; New York: 1991: 483
- 10b Pellissier H, Santelli M. Tetrahedron 2003; 59: 701
- 10c Chen Y, Larock RC. Arylation Reactions Involving the Formation of Arynes . In Modern Arylation Methods . Ackermann L. Wiley-VCH; New York: 2009. Chap. 12, 401
- 10d Wenk HH, Winkler M, Sander W. Angew. Chem. Int. Ed. 2003; 42: 502
- 10e Wu C, Shi F. Asian J. Org. Chem. 2013; 2: 116
- 11a Spiteri C, Keeling S, Moses JE. Org. Lett. 2010; 12: 3368
- 11b Wu C, Fang Y, Larock RC, Shi F. Org. Lett. 2010; 12: 2234
- 11c Kivrak A, Larock RC. J. Org. Chem. 2010; 75: 7381
- 11d Dubrovskiy AV, Larock RC. Org. Lett. 2010; 12: 1180
- 11e Spiteri C, Sharma P, Zhang F, Macdonald SJ. F, Keeling S, Moses JE. Chem. Commun. 2010; 46: 1272
- 11f Jin T, Yamamoto Y. Angew. Chem. Int. Ed. 2007; 46: 3323
- 11g Liu Z, Shi F, Martinez PD. G, Raminelli C, Larock RC. J. Org. Chem. 2008; 73: 219
- 11h Shi F, Waldo JP, Chen Y, Larock RC. Org. Lett. 2008; 10: 2409
- 11i Zhang F, Moses JE. Org. Lett. 2009; 11: 1587
- 11j Bronner SM, Bahnck KB, Garg NK. Org. Lett. 2009; 11: 1007
- 11k Huang X.-C, Liu Y.-L, Liang Y, Pi S.-F, Wang F, Li J.-H. Org. Lett. 2008; 10: 1525
- 11l Ren H, Wu C, Ding X, Chen X, Shi F. Org. Biomol. Chem. 2012; 10: 8975
- 12 Structural parameters for 3g: data collection: Rigaku Mercury CCD area detector; crystal size: 0.40 × 0.20 × 0.15 mm3; C20H30NO2, Mr = 316.45, monoclinic, space group P21/c, a = 11.550(4), b = 14.071(5), c = 21.111(8) Å, β = 96.766(5), V = 3407 (2) Å3, Z = 8, D calcd = 1.234 g cm–3, R[I > 2σ(I)] = 0.1774, wR[I > 2σ(I)] = 0.4292.
For selected examples, see:
For selected examples, see:
For books, see:
For reviews, see:
For selected examples, see:
For selected examples, see:
For reviews on the use of arynes in organic synthesis, see:
For recent selected examples in aryne 1,3-dipolar cycloadditions, see: