A Facile Route to H-Pyrazolo[5,1-a]isoquinolines through a Multicomponent Reaction of 2-Alkynylbenzaldehyde, Sulfonylhydrazine, and Benzyne

Jinming Yang; Xingxin Yu; Jie Wu

doi:10.1055/s-0033-1341102

Synthesis, Table of Contents

Synthesis 2014; 46(10): 1362-1366
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

Jinming Yang

^aSchool of Pharmacy, Yancheng Teachers University, Yancheng, Jiangsu 224051, P. R. of China

,

Xingxin Yu

^bDepartment of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China

,

Jie Wu*

^bDepartment of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China

^cState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China Fax: +86(21)65641740 Email: jie_wu@fudan.edu.cn

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Abstract

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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 - tosylhydrazine

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References

References and Notes

For selected examples, see:

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

For selected examples, see:

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

For books, see:

4a Terrett NK. Combinatorial Chemistry . Oxford University Press; New York: 1998
4b Zhu J, Bienaymé H. Multicomponent Reactions . Wiley-VCH; Weinheim: 2005

For reviews, see:

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

For selected examples, see:

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

For selected examples, see:

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

For reviews on the use of arynes in organic synthesis, see:

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

For recent selected examples in aryne 1,3-dipolar cycloadditions, see:

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.

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