Cyclization of Nitroacetamide Derivatives with a Tethered Phenyl Ring in Triflic Acid

Bamba Fanté; Yaya Soro; Sorho Siaka; Jérôme Marrot; Jean-Marie Coustard

doi:10.1055/s-0033-1340960

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(07): 969-974
DOI: 10.1055/s-0033-1340960

letter

Cyclization of Nitroacetamide Derivatives with a Tethered Phenyl Ring in Triflic Acid

Bamba Fanté*

^aLaboratoire de Chimie Organique Structurale, Université Félix Houphouët-Boigny, 22 BP 582 Abidjan 22, Côte d’Ivoire eMail: fante_bamba1@yahoo.fr

,

Yaya Soro

^bLaboratoire des Procédés Industriels de Synthèse, de l’Environnement et des Énergies Nouvelles, Institut National Polytechnique Félix Houphouët-Boigny, BP 991 Yamoussoukro, Côte d’Ivoire

,

Sorho Siaka

^bLaboratoire des Procédés Industriels de Synthèse, de l’Environnement et des Énergies Nouvelles, Institut National Polytechnique Félix Houphouët-Boigny, BP 991 Yamoussoukro, Côte d’Ivoire

,

Jérôme Marrot

^cLaboratoire ILV-UVSQ – UMR 8180 CNRS, 45 Avenue des États Unis, 78035 Versailles Cedex, France

,

Jean-Marie Coustard †

^dLaboratoire IC2MP-UMR 7285 CNRS, 40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France

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Abstract

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This publication is dedicated to the memory of Professor Jean-Marie Coustard who supervised this work but passed away at the end of August 2013. Rest in peace dear Professor.

Abstract

N-(3-Hydroxypropyl)-2-nitro-N-(ω-phenylalkyl)acetami-des underwent intramolecular cyclization in triflic acid to afford the corresponding hydroxyimino six- to nine-membered benzofused lactams. The six-membered derivative slowly transformed into 2-(3-hydroxypropyl)isoquinolin-3-one. NMR spectroscopic analysis in situ provided information on the cationic species involved in the reaction, permitting a mechanism to be postulated. This reaction provides a novel and simple route to benzofused lactams.

Key words

cations - protonation - cyclization - lactams - bicyclic compounds

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Referenzen

References and Notes
1 Kislyi VV, Samet AV, Semenov VV. Curr. Org. Chem. 2001; 5: 553
2 Kearny T, Harris PA, Jackson A, Joule JA. Synthesis 1992; 769
3 Manjunatha SG, Chittari P, Rajappa S. Helv. Chim. Acta 1991; 74: 1071

4a Coustard J.-M, Jacquesy J.-C, Violeau B. Tetrahedron Lett. 1991; 32: 3075
4b Ohwada T, Yamagata N, Shudo K. J. Am. Chem. Soc. 1991; 113: 1364

5 Hegarthy AF. Acc. Chem. Res. 1980; 13: 448
6 Coustard J.-M. Tetrahedron 1995; 51: 10929
7 Coustard J.-M. Tetrahedron 1996; 52: 9509
8 Coustard J.-M. Tetrahedron 1999; 55: 5809
9 Soro Y, Bamba F, Siaka S, Coustard J.-M. Tetrahedron Lett. 2006; 47: 3315

10a Coustard J.-M, Soro Y, Siaka S, Fanté B, Cousson A. Tetrahedron 2006; 62: 3320
10b Soro Y, Bamba F, Siaka S, Coustard J.-M, Adima AA. J. Chem. Sci. 2007; 119: 259

11 Coustard J.-M. Eur. J. Org. Chem. 2001; 1525

12a Cecchi L, De Sarlo F, Machetti F. Eur. J. Org. Chem. 2006; 21: 4852
12b Hao M.-H, Xiong Z, Aungst RA, Davis AL, Cogan D, Goldberg DR. US 20050245536, 2005

13a Manjunatha SG, Reddy KV, Rajappa S. Tetrahedron Lett. 1990; 31: 1327
13b Reddy TI, Bhawal BM, Rajappa S. Tetrahedron 1993; 19: 2101

14a Matsumura E, Ariga M, Tohda Y. Bull. Chem. Soc. Jpn. 1979; 52: 2413
14b Matsumura E, Ariga M, Tohda Y. Tetrahedron Lett. 1979; 20: 1393

15a Mano M, Seo T, Imai K.-I. Chem. Pharm. Bull. 1980; 28: 2720
15b Scardovi N, Casalini A, Peri F, Righi P. Org. Lett. 2002; 4: 965

16a Marson CM, Fallah F. Tetrahedron Lett. 1994; 35: 293
16b King FD, Caddick S. Tetrahedron Lett. 2011; 52: 6783
16c King FD, Caddick S. Org. Biomol. Chem. 2012; 10: 3244

17 Thorup N, Drier C, Simonsen O. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1981; 37: 1442

18a Manea VP, Wilson KJ, Cable JR. J. Am. Chem. Soc. 1997; 119: 2033
18b LaPlanche LA, Rogers MT. J. Am. Chem. Soc. 1964; 86: 337
18c Okamoto I, Nabeta M, Minami T, Nakashima A, Morita N, Takeya T, Masu H, Azumaya I, Tamura O. Tetrahedron Lett. 2007; 48: 573

19 Sheldrick GM. SHELXL-97, Program for the Refinement of Crystal Structures. University of Göttingen; Göttingen: 1997
20 APEX2 version 1.0-8 . Bruker AXS; Madison WI: 2003
21 SHELXTL version 6.14 . Bruker AXS; Madison WI: 2001
22 X-ray intensity data were collected on a Bruker X8-APEX2 CCD area-detector diffractometer using Mo Kα radiation (λ = 0.71073 Å). Three sets of narrow data frames (120 s per frame) were collected at different values of θ, for 1 and 2 initial values of φ and ω, respectively, using 0.5° increments of φ or ω. Data reduction was accomplished using SAINT V7.03.²⁰ The substantial redundancy in data allowed a semiempirical absorption correction (SADABS V2.10)²⁰ to be applied, on the basis of multiple measurements of equivalent reflections. The structure was solved by direct methods, developed by successive difference Fourier syntheses, and refined by full-matrix least-squares on all F ² data using SHELXTL V6.14.²¹ Hydrogen atoms were included in calculated positions and allowed to ride on their parent atoms. Crystal data, data collection, and processing parameters were deposited at the Cambridge Crystallographic Data Centre under the reference CCDC-875333.

23a Ohwada T, Ohta T, Shudo K. J. Am. Chem. Soc. 1986; 108: 3029
23b Ohwada T, Itai A, Ohta T, Shudo K. J. Am. Chem. Soc. 1987; 109: 7036
23c Olah GA, Fung AP, Rawdah TN. J. Org. Chem. 1980; 45: 4149

24a Gillespie RJ, Birchall T. Can. J. Chem. 1963; 41: 148
24b Olah GA, White AM, Ku AT. J. Org. Chem. 1971; 36: 3585

25 Favier I, Duñach E. Tetrahedron Lett. 2004; 45: 3393
26 Olah GA, Sommer J, Namanworth E. J. Am. Chem. Soc. 1967; 89: 3576

27a Jacquesy JC In Carbocation Chemistry . Olah GA, Prakash GK. S. John Wiley and Sons; New York: 2004: 359-376
27b Fahy J, Duflos A, Ribert J.-P, Jacquesy J.-C, Berrier C, Jouannetaud M.-P, Zunino F. J. Am. Chem. Soc. 1997; 119: 8576

28a Sai KK. S, O’Connor MJ, Klumpp DA. Tetrahedron Lett. 2011; 52: 2195
28b O’Connor MJ, Boblak KN, Topinka MJ, Kindelin PJ, Briski JM, Zheng C, Klumpp DA. J. Am. Chem. Soc. 2010; 132: 3266
28c Klumpp DA, Rendy R, Zhang Y, Gomez A, McElrea A. Org. Lett. 2004; 6: 1789
28d Olah GA, Klumpp DA. Acc. Chem. Res. 2004; 37: 211

29a Watthey JW. H. US 4,470,988, 1984
29b Parsons WH, Patchett AA, Thorsett ED. US 4873235, 1998
29c Zhao H, Thurkauf A. WO 0076981, 2000

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