Copper-Catalyzed Tandem Reactions of 2-Iodobenzamides with Sodium Azide: An Efficient Synthesis of [1,2,3]Triazolo[1,5-a][1,4]-benzodiazepin-6(5H)-ones

Wanli Chen; Haitao Li; Xiaoling Gu; Yinghong Zhu

doi:10.1055/s-0034-1380120

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(06): 785-790
DOI: 10.1055/s-0034-1380120

letter

Copper-Catalyzed Tandem Reactions of 2-Iodobenzamides with Sodium Azide: An Efficient Synthesis of [1,2,3]Triazolo[1,5-a][1,4]-benzodiazepin-6(5H)-ones

Wanli Chen

^aCenter of Analysis & Measurement, Zhejiang University of Technology, Hangzhou 310014, P. R. of China,

,

Haitao Li

^aCenter of Analysis & Measurement, Zhejiang University of Technology, Hangzhou 310014, P. R. of China,

,

Xiaoling Gu

^aCenter of Analysis & Measurement, Zhejiang University of Technology, Hangzhou 310014, P. R. of China,

,

Yinghong Zhu*

^bCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China eMail: yhzhuchem@zjut.edu.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Copper-catalyzed tandem reactions between 2-iodobenzamides with a propargyl group on the nitrogen atom moiety and sodium azide are presented, providing an efficient method for the synthesis of 3-substituted [1,2,3]triazolo[1,5-a][1,4]benzodiazepin-6(5H)-ones under mild conditions in moderate yields.

Key words

tandem reactions - copper-catalyzed - [1,2,3]triazolo[1,5-a][1,4]benzodiazepin-6(5H)-one - 2-iodobenzamides -

Volltext

Referenzen

References and Notes

1a Kaneko T, Wong H, Doyle TW, Rose WC, Bradner WT. J. Med. Chem. 1985; 28: 388
1b Zhang W, William JP, Lu Y, Nagashima T, Chu Q. Tetrahedron Lett. 2007; 48: 563
1c Keenam RM, Callaham JF, Samanen JM, Bondinell WE, Calvo RR, Chen I, DeBrosse C, Eggleston DS, Haltiwanger RC, Hwang SM, Jakes DR, Ku TW, Miller WH, Newlander KA, Nichols A, Parker MF, Southhall LS, Uzinskas I, Vasko-Moser JA, Venslavsky JW, Wong AS, Huffmann WF. J. Med. Chem. 1999; 42: 545
1d Novelli F, Sparatore A, Tass B, Sparatore F. Bioorg. Med. Chem. Lett. 1999; 9: 3031
1e Sugimori T, Okawa T, Eguchi S, Kakehi A, Yashima E, Okamoto Y. Tetrahedron 1998; 54: 7997
1f Walser A, Fryer RI. Bicyclic Diazepines, In Chemistry of Heterocyclic Compounds, . Taylor EC, Weissberger A. Wiley; Chichester: 1991. Part 431, Vol. 50 Chap. V-VIII

2a Roger-Evans M, Spurr P, Hennig M. Tetrahedron Lett. 2003; 44: 2425
2b Broggini G, Orlandi M, Turconi A, Zoni C. Org. Prep. Proced. Int. 2003; 35: 609
2c Broggini G, Molteni G, Terraneo A, Zecchi G. Tetrahedron 1999; 55: 14803
2d Gu Z.-Q, Wong G, Dominguez C, de Costa BR, Rice KC, Skolnick P. J. Med. Chem. 1993; 36: 1001

3 Ogawa K, Matsushita Y. Chem. Pharm. Bull. 1992; 40: 2442
4 Donohue AR, Dannals RF. Tetrahedron Lett. 2009; 50: 7271

5a Basolo L, Beccalli EM, Borsini E, Gianluigi Broggini G, Maisaa Khansaa M, Rigamonti M. Eur. J. Org. Chem. 2010; 1694
5b Patel N, Chambers CS, Hemming K. Synlett 2009; 3043
5c Broggini G, Marchi ID, Martinelli M, Paladino G, Pilati T, Terraneo A. Synthesis 2005; 2246
5d Hunkeler W. Chimia 1993; 47: 141

6a Sahoo S, Veliyath SK, Mahendra Kumar CB. Int. J. Res. Pharm. Sci. 2012; 3: 326
6b Majumdar KC, Ray K. Synthesis 2011; 3767
6c Genin MJ, Allwine DA, Anderson DJ, Barbachyn MR, Emmert DE, Garmon SA, Graber DR, Grege KC, Hester JB, Hutchinson DK, Morris J, Reischer RJ, Ford CW, Zurenko GE, Hamel JC, Schaadt RD, Stapert D, Yagi BH. J. Med. Chem. 2000; 43: 953
6d Palhagen S, Canger R, Henriksen O, van Parys JA, Riviere M.-E, Karolchyk MA. Epilepsy Res. 2001; 43 115
6e Fan WQ, Katritzky AR In Comprehensive Heterocyclic Chemistry II . Vol. 4. Katritzky AR, Rees CW, Scriven EF. V. Elsevier; Oxford: 1996: 1-26
6f Alvarez R, Velásquez S, San-Félix A, Aquaro S, De Clercq E, Perno C.-F, Karlsson A, Balzarini J, Camarasa MJ. J. Med. Chem. 1994; 37: 4185

7a Majumdar KC, Ganai S. Synthesis 2013; 45: 2619
7b Thomas AW. Bioorg. Med. Chem. Lett. 2002; 12: 1881
7c Alajarin M, Cabrera J, Pastor A, Villalgordo JM. Tetrahedron Lett. 2007; 48: 3495
7d Akritopoulou-Zanze I, Gracias V, Djuric SW. Tetrahedron Lett. 2004; 45: 8439
7e Coffen DL, Fryer RI, Katonak DA, Wong F. J. Org. Chem. 1975; 40: 894
7f Broggini G, Molteni G, Terraneo A, Zecchi G. Tetrahedron 1999; 55: 14803
7g Broggini G, DeMarchi I, Martinelli M, Paladino G, Pilati T, Terraneo A. Synthesis 2005; 2246

8 Chowdhury C, Sasmal AK, Achari B. Org. Biomol. Chem. 2010; 8: 4971
9 Broggini G, Molteni G, Zecchi G. Synthesis 1995; 647

For reviews about CuAAC reactions and its applications, see:

10a Agalave SG, Maujan SR, Pore VS. Chem. Asian J. 2011; 6: 2696
10b Aragão-Leoneti V, Campo VL, Gomes AS, Field RA, Carvalho I. Tetrahedron 2010; 66: 9475
10c Franc G, Kakkar AK. Chem. Soc. Rev. 2010; 39: 1539
10d Iha RK, Wooley KL, Nyström AM, Burke DJ, Kade MJ, Hawker CJ. Chem. Rev. 2009; 109: 5620
10e Amblard F, Cho JH, Schinazi RF. Chem. Rev. 2009; 109: 4207
10f Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 2951

For some recent reviews about copper-catalyzed Ullmann-type coupling reactions, see:

11a Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
11b Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337
11c Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
11d Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
11e Ma D, Cai Q. Acc. Chem. Res. 2008; 41: 1450
11f Surry DS, Buchwald SL. Chem. Sci. 2010; 1: 13

For some selected examples, see:

12a Feldman AK, Colasson B, Fokin VV. Org. Lett. 2004; 6: 3897
12b Alonso F, Moglie Y, Radivoy G, Yus M. J. Org. Chem. 2011; 76: 8394
12c Li W.-T, Wu W.-H, Tang C.-H, Tai R, Chen S.-T. ACS Comb. Sci. 2011; 13: 72
12d Attanasi OA, Favi G, Filippone P, Mantellini F, Moscatelli G, Perrulli FR. Org. Lett. 2010; 12: 468
12e Reddy PS, Sreedhar B. Synthesis 2009; 4203
12f Kumar D, Reddy VB, Varma RS. Tetrahedron Lett. 2009; 50: 2065
12g Ackermann L, Potukuchi HK, Landsberg D, Vicente R. Org. Lett. 2008; 10: 3081
12h Yan J, Zhou F, Qin D, Cai T, Ding K, Cai Q. Org. Lett. 2012; 14: 1262
12i Cai Q, Yan J, Ding K. Org. Lett. 2012; 14: 3332

13a Chen W, Cui J, Zhu Y, Hu X, Mo W. J. Org. Chem. 2012; 77: 1585
13b Chen W, Jin L, Zhu Y, Cao X, Zheng L, Mo W. Synlett 2013; 24: 1856

14 3,5-Diphenyl-4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]-diazepin-6(5H)-one (4a); Typical Procedure 2-Iodobenzamides 5 (0.3 mmol), NaN₃ (0.36 mmol), CuI (0.03 mmol), N,N′-dimethylethylenediamine (0.06 mmol), and DMSO (1 mL) and H₂O (0.2 mL) were added into a Schlenk tube at r.t. under N₂. The reaction mixture was stirred at 90 °C until the reaction was complete, as monitored by TLC. Then the reaction mixture was cooled, H₂O was added, the aqueous layer was extracted with CH₂Cl₂ (3 × 20 mL), and dried over MgSO₄. After filtration and removal of the solvent in vacuo, the residues were purified with flash chromatography (silica gel; PE–EtOAc, 4:1 v/v) to afford 4 as a yellow solid; mp 208–210 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.19 (d, J = 7.7 Hz, 1 H), 8.12 (d, J = 8.0 Hz, 1 H), 7.78 (t, J = 7.4 Hz, 1 H), 7.63 (t, J = 7.6 Hz, 1 H), 7.45–7.40 (m, 4 H), 7.36–7.34 (m, 4 H), 7.26 (d, J = 7.6 Hz, 2 H), 5.00 (s, 2 H). ¹³C NMR (125 MHz, CDCl₃): δ = 166.1, 143.6, 142.1, 133.2, 132.9, 132.6, 130.7, 129.7, 129.6, 129.3, 129.0, 128.7, 127.8, 127.4, 127.2, 126.3, 122.7, 43.8. IR: 1643, 1492, 1403, 753, 695 cm^–1. ESI-HRMS: m/z calcd for C₂₂H₁₇N₄O [M + H]⁺: 353.1397; found: 353.1412.

Zusatzmaterial

Supporting Information