Rapid Access to H-Pyrazolo[5,1-a]isoquinolines
via Sequential Reaction of N′-(2-Alkynylbenzylidene)hydrazides

Zhiyuan Chen; Xiaolin Pan; Jie Wu

doi:10.1055/s-0030-1259704

LETTER

Rapid Access to H-Pyrazolo[5,1-a]isoquinolines via Sequential Reaction of N′-(2-Alkynylbenzylidene)hydrazides

Zhiyuan Chen^a, Xiaolin Pan^a, Jie Wu*^a,b
^a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Fax: +86(21)65641740; e-Mail: jie_wu@fudan.edu.cn;
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

Diverse H-pyrazolo[5,1-a]isoquinolines are efficiently synthesized via sequential reaction of N′-(2-alkynylbenzylidene)hydrazides. Bromo-containing isoquinolinium, generated from N′-(2-alkynylbenzylidene)hydrazide with bromine, reacts with α,β-unsaturated aldehyde and methanol under mild conditions, leading to 6-bromo-1-(methoxymethyl)-H-pyrazolo[5,1-a]isoquinolines in moderate to good yields. Further elaboration via palladium catalyzed Suzuki-Miyaura coupling or Heck reaction produces diverse H-pyrazolo[5,1-a]isoquinoline compounds.

Key words

alkynes - hydrazide - bromine - methanol - isoquinoline - α,β-unsaturated aldehyde

Volltext

Referenzen

References and Notes

For selected examples of multi-component reactions, see:

1a Multicomponent Reactions Zhu J. Bienayme H. Wiley-VCH; Weinheim: Germany, 2005.

1b Ramon DJ. Yus M. Angew. Chem. Int. Ed. 2005, 44: 1602

1c Nair V. Rajesh C. Vinod AU. Bindu S. Sreekenth AR. Balagopal L. Acc. Chem. Res. 2003, 36: 899

1d Orru RVA. de Greef M. Synthesis 2003, 1471

1e Balme G. Bossharth E. Monteiro N. Eur. J. Org. Chem. 2003, 4101

1f Dömling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168

1g Bienaymé H. Hulme C. Oddon G. Schmitt P. Chem. Eur. J. 2000, 6: 3321

1h Sunderhaus JD. Martin SF. Chem. Eur. J. 2009, 15: 1300

1i Ugi I. Domling A. Werner B. J. Heterocycl. Chem. 2000, 37: 647

1j Zhu J. Eur. J. Org. Chem. 2003, 1133

1k Hulme C. Gore V. Curr. Med. Chem. 2003, 10: 51

1l Weber L. Curr. Med. Chem. 2002, 9: 1241

2a Walsh DP. Chang Y.-T. Chem. Rev. 2006, 106: 24

2b Arya P. Chou DTH. Baek M.-G. Angew. Chem. Int. Ed. 2001, 40: 339

2c Schreiber SL. Science 2000, 287: 1964

For selected examples, see:

3a Ye S. Yang X. Wu J. Chem. Commun. 2010, 46: 2950

3b Yu X. Chen Z. Yang X. Wu J. J. Comb. Chem. 2010, 12: 374

3c Yu X. Wu J. J. Comb. Chem. 2010, 12: 238

3d Ye S. Gao K. Zhou H. Yang X. Wu J. Chem. Commun. 2009, 5406

3e Chen Z. Yang X. Wu J. Chem. Commun. 2009, 3469

3f Chen Z. Yu X. Su M. Yang X. Wu J. Adv. Synth. Catal. 2009, 351: 2702

3g Chen Z. Ding Q. Yu X. Wu J. Adv. Synth. Catal. 2009, 351: 1692

3h Ding Q. Wang Z. Wu J. J. Org. Chem. 2009, 74: 921

3i Yu X. Wu J.
J. Comb. Chem. 2009, 11: 895

3j Chen Z. Su M. Yu X. Wu J. Org. Biomol. Chem. 2009, 7: 4641

3k Yu X. Ye S. Wu J. Adv. Synth. Catal. 2010, 352: 2050

3l Ye S. Yang X. Wu J. Chem. Commun. 2010, 46: 5238

For selected examples, see:

4a Chen Z. Wu J. Org. Lett. 2010, 12: 4856

4b Qiu G. Ding Q. Ren H. Peng Y. Wu J. Org. Lett. 2010, 12: 3975

4c Ye S. Gao K. Wu J. Adv. Synth. Catal. 2010, 352: 1746

4d Ye S. Ren H. Wu J. J. Comb. Chem. 2010, 12: 670

4e Yu X. Ding Q. Wu J. J. Comb. Chem. 2010, 12: 743

4f Ren H. Ye S. Liu F. Wu J. Tetrahedron 2010, 66: 8242

4g Chen Z. Yu X. Wu J. Chem. Commun. 2010, 46: 6356

4h Ding Q. Wu J. Org. Lett. 2007, 9: 4959

4i Gao K. Wu J. J. Org. Chem. 2007, 72: 8611

4j Sun W. Ding Q. Sun X. Fan R. Wu J. J. Comb. Chem. 2007, 9: 690

5a Bailly C. Curr. Med. Chem. Anti-Cancer Agents 2004, 4: 363

5b Marco E. Laine W. Tardy C. Lansiaux A. Iwao M. Ishibashi F. Bailly C. Gago F. J. Med. Chem. 2005, 48: 3796

5c Reddy MVR. Rao MR. Rhodes D. Hansen MST. Rubins K. Bushman FD. Venkateswarlu Y. Faulkner DJ. J. Med. Chem. 1999, 42: 1901

5d Aubry A. Pan X.-S. Fisher LM. Jarlier V. Cambau E. Antimicrob. Agents Chemother. 2004, 48: 1281

6a Lober S. Hubner H. Gmeiner P. Bioorg. Med. Chem. Lett. 2002, 12: 2377

6b Hasen JB. Weis J. Suzdak PD. Eskesen K. Bioorg. Med. Chem. Lett. 1994, 4: 695

6c Bettinetti L. Schlotter K. Hubner H. Gmeiner P. J. Med. Chem. 2002, 45: 4594

7a Johns BA. Gudmundsson KS. Turner EM. Allen SH. Samano VA. Ray JA. Freeman GA. Boyd FL. Sexton CJ. Selleseth DW. Creech KL. Moniri KR. Bioorg. Med. Chem. 2005, 13: 2397

7b Akahane A. Katayama H. Mitsunaga T. Kato T. Kinoshita T. Kita Y. Kusunoki T. Terai T. Yoshida K. Shiokawa Y. J. Med. Chem. 1999, 42: 779

7c Kuroda S. Akahane A. Itani H. Nishimura S. Durkin K. Kinoshita T. Tenda Y. Sakane K. Bioorg. Med. Chem. Lett. 1999, 9: 1979

8 Ding Q. Chen Z. Yu X. Peng Y. Wu J. Tetrahedron Lett. 2009, 50: 340

For reviews, see:

9a Miyaura N. Top. Curr. Chem. 2002, 219: 11

9b Suzuki A. J. Organomet. Chem. 1999, 576: 147

9c Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176

9d De Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions 2nd ed.: John Wiley & Sons; Weinheim, Germany: 2004.

Zusatzmaterial

Supporting Information