Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2013; 45(22): 3173-3178
DOI: 10.1055/s-0033-1338530
DOI: 10.1055/s-0033-1338530
paper
Synthesis of a Naphtho-pyrido-Annulated Iodonium Salt and Pd-Catalyzed Transformation to 7H-Naphtho[1,8-bc][1,5]naphthyridine
Authors
Further Information
Publication History
Received: 23 June 2013
Accepted after revision: 22 August 2013
Publication Date:
18 September 2013 (online)
Dedicated to Heinz Kolshorn on the occasion of his 70th birthday
Abstract
Nitropyridylnaphthalene is the central intermediate for the synthesis of naphthonaphthyridine and benzo-δ-carboline. Whereas the Cadogan reaction gives the carboline, transformation of the nitro group to iodo followed by oxidation and cyclization results in an iodonium salt. A twofold Pd-catalyzed amination leads to the naphthyridine.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information (PDF)
-
References
- 1a Kapil RS. The Alkaloids 1971; 13: 273
- 1b Chakraborty DP, Roy S. Progress in the Organic Chemistry of Natural Products . Vol. 57. Springer; Wien: 1991: 71
- 1c Knölker HJ, Reddy KP. Chem. Rev. 2002; 102: 4303
- 1d Knölker HJ. Top. Curr. Chem. 2005; 244: 115
- 1e Molinski TF. Chem. Rev. 1993; 93: 1825
- 2a Borsche W, Witte A, Bothe W. Justus Liebigs Ann. Chem. 1908; 359: 49
- 2b Bucherer HT, Seyde F. J. Prakt. Chem. 1908; 77: 403
- 2c Pindur U, Erfanaian-Abdoust H. Chem. Rev. 1989; 89: 1681
- 2d Moody CJ, Shah P. J. Chem. Soc., Perkin Trans. 1 1989; 2463
- 2e Graebe C, Ullmann F. Justus Liebigs Ann. Chem. 1896; 291: 16
- 2f Cadogan JI. G. Synthesis 1969; 11
- 2g Katritzky AR, Pozharskii AF. Handbook of Heterocyclic Chemistry . Pergamon; Oxford: 2000. 2nd ed. 657
- 2h Merisor E, Conrad J, Klaiber I, Mika S, Beifuss U. Angew. Chem. Int. Ed. 2007; 46: 3353
- 2i Merisor E, Conrad J, Klaiber I, Mika S, Beifuss U. Synlett 2007; 2033
- 2j Rajanarendar E, Reddy AS. R, Shaik FP. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008; 47: 1591
- 3a Dassonneville B, Witulski B, Detert H. Eur. J. Org. Chem. 2011; 2836
- 3b Nissen F, Detert H. Eur. J. Org. Chem. 2011; 2845
- 4 Letessier J, Detert H, Götz K, Opatz T. Synthesis 2012; 44: 747
- 5a Letessier J, Detert H. Synthesis 2012; 44: 290
- 5b Letessier J, Schollmeyer D, Detert H. Acta Crystallogr., Sect. E 2011; 67: o2341
- 5c Letessier J, Schollmeyer D, Detert H. Acta Crystallogr., Sect. E 2011; 67: o2494
- 6a Behringer FM, Forgione PS, Yudis MD. Tetrahedron 1960; 8: 49
- 6b Chen Z.-C, Jin Y.-Y, Stang PJ. J. Org. Chem. 1987; 52: 4115
- 6c Gao P, Portoghese PS. J. Org. Chem. 1995; 60: 2276
- 6d Phipps RJ, Gaunt MJ. Science (Washington, D.C.) 2009; 323: 1593
- 6e Zhu M, Zhou Z, Chen R. Synthesis 2008; 2680
- 6f Rhadakrisnan U, Stang PJ. Org. Lett. 2001; 3: 859
- 6g Zhu M, Song Y, Cao Y. Synthesis 2007; 912
- 6h Hellwinkel D, Schenk W, Blaicher W. Chem. Ber. 1978; 111: 1798
- 6i Vancikov AN, Bobyleva MS, Komissarova EE, Kulikov NS, Tolstaya TP. Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 1998; 34: 371
- 6j Ptitsyna OA, Lyatiev GG, Reutov OA. Zh. Org. Khim. 1970; 6: 1353
- 7a Behringer FM, Bierley A, Drexler M, Gindler EM, Lumpkin CC. J. Am. Chem. Soc. 1953; 75: 2708
- 7b Marsach G, Steunutz R, Bergman A. Eur. J. Org. Chem. 2003; 2566
- 7c Caroll MA, Wood RA. Tetrahedron 2007; 63: 11349
- 7d Liang Y, Luo S, Liu C, Wu X, Ma Y. Tetrahedron 2000; 56: 2961
- 7e Kang S.-K, Lee S.-H, Lee D. Synlett 2000; 1022
- 8a Hartwig JF. Angew. Chem. Int. Ed. 1998; 37: 2046
- 8b Muci AR, Buchwald SL. Top. Curr. Chem. 2002; 219: 131
- 9a Bunjyan PJ, Cadogan JI. G. J. Chem. Soc. 1963; 42
- 9b Cadogan JI. G. Q. Rev. Chem. Soc. 1962; 16: 208
- 9c Cadogan JI. G, Cameron-Wood M, Mackie RK, Searle RJ. J. Chem. Soc. 1965; 4831
- 10a Wrobel N, Witulski B, Schollmeyer D, Detert H. Acta Crystallogr., Sect. E 2013; 69: o69
- 10b Wrobel N, Witulski B, Schollmeyer D, Detert H. Acta Crystallogr., Sect. E 2013; 69: o116
- 11 Wrobel N, Schollmeyer D, Detert H. Acta Crystallogr., Sect. E 2012; 68: o1249
- 12a Beringer FM, Chang LL. J. Org. Chem. 1971; 36: 4055
- 12b Koser GF, Wettach RH. J. Org. Chem. 1980; 45: 1542
- 12c Peacock MJ, Pletcher D. Tetrahedron Lett. 2000; 41: 8995
- 12d Whitesides GM, Eisenhut M, Bunting WM. J. Am. Chem. Soc. 1974; 96: 5398
- 13a Collette J, McGreer D, Crawford R, Chubb F, Sandin RR. J. Am. Chem. Soc. 1956; 78: 3819
- 13b Beringer FM, Kravetz L, Topliss GB. J. Org. Chem. 1965; 30: 1141
- 14 Peng H, Chen X, Chen Y, He Q, Xie Y, Yang C. Tetrahedron 2011; 67: 5725
Reference Ris Wihthout Link
- 15 Batsanov AS, Petrov VN, Struchkov YuT, Egorova LD, Lisichkina IN, Tolstaya TP. Izv. Akad. Nauk SSSR, Ser. Khim. 1985; 190: 2309
- 16 Meier C, Sömmer P, Girreser U, Clement B. Synthesis 2013; 45: 893
- 17a Sheldrick GM. SHELXL97, Program for Crystal Structure Refinement . University of Göttingen; Germany: 1997
- 17b CCDC-891469 (7) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.