Intramolecular Cycloaddition Approach to Fused Pyrazoles: Access to 4,5-Dihydro-2H-pyrazolo[4,3-c]quinolines, 2,8-Dihydroindeno[2,1-c]pyrazoles, and 4,5-Dihydro-2H-benzo[e]indazoles

Moumita Jash; Bimolendu Das; Suparna Sen; Chinmay Chowdhury

doi:10.1055/s-0036-1591737

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(07): 1511-1520
DOI: 10.1055/s-0036-1591737

paper

Intramolecular Cycloaddition Approach to Fused Pyrazoles: Access to 4,5-Dihydro-2H-pyrazolo[4,3-c]quinolines, 2,8-Dihydroindeno[2,1-c]pyrazoles, and 4,5-Dihydro-2H-benzo[e]indazoles

Autor*innen

Moumita Jash

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in
Bimolendu Das

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in
Suparna Sen

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in
Chinmay Chowdhury*

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in

Abstract

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Abstract

A straightforward and efficient method for the synthesis of pyrazoles fused with 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1H-indene, or 1,2,3,4-tetrahydronaphthalene involves the formation of the tosylhydrazone from an aromatic substrate carrying aldehyde and acetylenic functionalities at appropriate positions, followed by base-promoted generation of the diazo compound and subsequent intramolecular 1,3-dipolar cycloaddition. A number of functional groups were found to be compatible for this reaction sequence and yields were moderate to very good (44–95%). A plausible reaction mechanism supported by DFT calculations has been provided to explain the formation of products.

Key words

cycloaddition - pyrazole - indazole - dihydroquinoline - quinoline

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Referenzen

References

1a Khan MF. Alam MM. Verma G. Akhtar W. Akhter M. Shaquiquzzaman M. Eur. J. Med. Chem. 2016; 120: 170
1b Kumar H. Saini D. Jai S. Jain N. Eur. J. Med. Chem. 2013; 70: 248
1c Küçükgüzel ŞG. Şenkardeş S. Eur. J. Med. Chem. 2015; 97: 786
1d McDonald E. Jones K. Brough PA. Drysdale MJ. Workman P. Curr. Top. Med. Chem. 2006; 6: 1193

2 Kumar V. Kaur K. Gupta GK. Sharma AK. Eur. J. Med.Chem. 2013; 69: 735

For example:

3a Celecoxib, a COX-2 inhibitor: Hassan GS. Abou-Seri SM. Kamel G. Ali MM. Eur. J. Med. Chem. 2014; 76: 482
3b Fezolamine, an antidepressant: Luttinger D. Hlasta DJ. Annu. Rep. Med. Chem. 1987; 22: 21
3c Difenamizole, an analgesic: Kameyama T. Nabeshima T. Neuropharmacology 1978; 17: 249

4a For anticancer activity: Wentland PM. U.S. Patent 5,334,595, 1994
4b For selective cyclooxygenase-2 (COX-2) inhibitory: Baruah B. Dasu K. Vaitilingam B. Vanguri A. Casturi SR. Yeleswarapu KR. Bioorg. Med. Chem. Lett. 2004; 14: 445
4c For A3 adenosine receptor antagonistic: Baraldi PG. Tabrizi MA. Preti D. Bovero Fruttarolo F. Romagnoli R. Zaid NA. Moorman AR. Varani K. Borea PA. J. Med. Chem. 2005; 48: 5001
4d For phosphodiesterase-4 (PDE4) inhibitory activity: Crespo MI. Gracia J. Puig C. Vega A. Bou J. Beleta J. Domenech T. Ryder H. Segarra V. Palacios JM. Bioorg. Med. Chem. Lett. 2000; 10: 2661
4e For antiulcer activity: Kalayanov GD. Kang SK. Cheon HG. Lee SG. Yum EK. Kim SS. Choi JK. Bull. Korean Chem. Soc. 1998; 19: 667
4f For γ-secretase inhibitory activity: Truong AP. Aubele DL. Probst GD. Neitzel ML. Semko CM. Bowers S. Dressen D. Hom RK. Konradi AW. Sham HL. Garofalo AW. Keim PS. Wu J. Dappen MS. Wong K. Goldbach E. Quinn KP. Sauer J.-M. Brigham EF. Wallace W. Nguyen L. Hemphill SS. Bova MP. Basi G. Bioorg. Med. Chem. Lett. 2009; 19: 4920

5a Skotnicki JS. Gilman CS. Steinbaugh BA. Musser JH. U.S. Patent 4,748,246, 1988 ; Chem. Abstr. 1988, 109, 110425u
5b Probst G. Aubele DL. Bowers S. Dressen D. Garofalo AW. Hom RK. Konradi AW. Marugg JL. Mattson MN. Neitzel ML. Semko CM. Sham HL. Smith J. Sun M. Truong AP. Ye XM. Xu Y.-Z. Dappen MS. Jagodzinski JJ. Keim PS. Peterson B. Latimer LH. Quincy D. Wu J. Goldbach E. Ness DK. Quinn KP. Sauer J.-M. Wong K. Zhang H. Zmolek W. Brigham EF. Kholodenko D. Hu K. Kwong GT. Lee M. Liao A. Motter RN. Sacayon P. Santiago P. Willits C. Bard F. Bova MP. Hemphill SS. Nguyen L. Ruslim L. Tanaka K. Tanaka P. Wallace W. Yednock TA. Basi GS. J. Med. Chem. 2013; 56: 5261

6a Murineddu G. Asproni B. Ruiu S. Deligia F. Falzoi M. Pau A. Thomas BF. Zhang Y. Pinna GA. Pani L. Lazzari P. Open Med. Chem. J. 2012; 6: 1
6b Minegishi H. Fukashiro S. Ban HS. Nakamura H. ACS Med. Chem. Lett. 2013; 4: 297
6c Liu Y.-N. Wang J.-J. Ji Y.-T. Zhao G.-D. Tang L.-Q. Zhang C.-M. Guo X.-L. Liu Z.-P. J. Med. Chem. 2016; 59: 5341
6d Schenone S. Bruno O. Ranise A. Brullo C. Bondavalli F. Filippelli W. Mazzeo F. Capuano A. Falcone G. Farmaco 2003; 58: 845
6e Meyers MJ. Arhancet GB. Hockerman SL. Chen X. Long SA. Mahoney MW. Rico JR. Garland DJ. Blinn JR. Collins JT. Yang S. Huang H.-C. McGee KF. Wendling JM. Dietz JD. Payne MA. Homer BL. Heron MI. Reitz DB. Hu X. J. Med. Chem. 2010; 53: 5979

7a Jash M. Das B. Chowdhury C. J. Org. Chem. 2016; 81: 10987
7b Kundu P. Mondal A. Chowdhury C. J. Org. Chem. 2016; 81: 6596
7c Kundu P. Mondal A. Das B. Chowdhury C. Adv. Synth. Catal. 2015; 357: 3737
7d Chowdhury C. Das B. Mukherjee S. Achari B. J. Org. Chem. 2012; 77: 5108

For a recent review, see:

8a Mekheimer RA. Ahmed EA. Sadek KU. Tetrahedron 2012; 68: 1637
8b Alizadeh A. Moafi L. Ghanbaripour R. Abadi MH. Zhu Z. Kubicki M. Tetrahedron 2015; 71: 3495
8c Maluleka MM. Mphahlele MJ. Tetrahedron 2013; 69: 699
8d Rivilli MJ. L. Moyano EL. Yranzo GI. Tetrahedron Lett. 2010; 51: 478
8e Duggineni S. Sawant D. Saha B. Kundu B. Tetrahedron 2006; 62: 3228
8f Kasiotis KM. Fokialakis N. Haroutounian SA. Synthesis 2006; 1791

9 Divya KV. L. Meena A. Suja TD. Synthesis 2016; 48: 4207

For structural isomers of dihydroindeno[2,1-c]pyrazoles 6, see:

10a Zheng Y. Zhang X. Yao R. Wen YC. Huang J. Xu X. J. Org. Chem. 2016; 81: 11072
10b Mor S. Nagoria S. Kumar A. Monga J. Lohan S. Med. Chem. Res. 2016; 25: 1096
10c Hamilton RW. J. Heterocycl. Chem. 1976; 13: 545

For structural isomers of 4,5-dihydrobenzo[e]indazoles 7, see:

11a Péréz-Aguilar MC. Valdés C. Angew. Chem. Int. Ed. 2013; 52: 7219

For structurally related compounds of 7, see:

11b Yang W. Ye S. Fanning D. Coon T. Schmidt Y. Krenitsky P. Stamos D. Yu J.-Q. Angew. Chem. Int. Ed. 2015; 54: 2501
11c Sivaprasad G. Sridhar R. Perumal PT. J. Heterocycl. Chem. 2006; 43: 389

12a Wu L.-L. Ge Y.-C. He T. Zhang L. Fu X.-L. Fu H.-Y. Chen H. Li R.-X. Synthesis 2012; 44: 1577
12b Aggarwal VK. de Vicente J. Bonnert RV. J. Org. Chem. 2003; 68: 5381
12c Péréz-Aguilar MC. Valdés C. Angew. Chem. Int. Ed. 2015; 54: 13729
12d Kong Y. Tang M. Wang Y. Org. Lett. 2014; 16: 576

13 Interestingly, it was observed that product 5f exists with its tautomeric form 5′f (see Scheme 3) in a ratio of 10:8 when NMR is recorded in DMSO-d ₆; in CDCl₃ this tautomerization appears to be blocked and 5f exists as a single isomer. This happens because dimethyl sulfoxide is possibly capable of making hydrogen bond with pyrazole NH leading to tautomerization.
14 CCDC 1537223 (5d), CCDC 1537224 (5e), CCDC 1537225 (6b) and CCDC 1537226 (6d) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
15 Savchenko TI. Silin OV. Kovalenko SM. Musatov VI. Nikitchenko VM. Ivachtchenko AV. Synth. Commun. 2007; 37: 1321

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