An Efficient Synthesis of Isoindolo[2,1-a]quinoline Derivatives via Imino Diels-Alder and Intramolecular Diels-Alder Reactions with Furan

Vladimir V. Kouznetsov; Uriel Mora Cruz; Fedor I. Zubkov; Eugenia V. Nikitina

doi:10.1055/s-2007-965875

PAPER

An Efficient Synthesis of Isoindolo[2,1-a]quinoline Derivatives via Imino Diels-Alder and Intramolecular Diels-Alder Reactions with Furan

Vladimir V. Kouznetsov*^a, Uriel Mora Cruz^a, Fedor I. Zubkov*^b, Eugenia V. Nikitina^b
^a Laboratorio de Química Orgánica y Biomolecular, CIBIMOL, Escuela de Química, Universidad Industrial de Santander, A.A. 678, Bucaramanga, Colombia
Fax: +57(7)6349069; e-Mail: kouznet@uis.edu.co;
^b Organic Chemistry Department of the Russian Peoples Friendship University, 6 Miklukho-Maklayia St, Moscow, 117198, Russian Federation
Fax: +7(495)9550779; e-Mail: fzubkov@sci.pfu.edu.ru;

Abstract

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Abstract

The straightforward synthesis of new isoindolo[2,1-a]quinoline derivatives from 2,4-disubstituted 1,2,3,4-tetrahydroquinolines bearing a furan fragment via the intramolecular Diels-Alder reaction is reported. The synthesis of key precursors was realized with excellent levels of diastereoselectivity either by Povarov reaction or by a multicomponent condensation approach.

Key words

Povarov reaction - quinolines - furans - intramolecular Diels-Alder reaction - isoindolo[2,1-a]quinolines

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References

<A NAME="RZ19006SS-1">1</A> Katritzky AR. Rachwal S. Rachwal B. Tetrahedron 1996, 52: 15031

<A NAME="RZ19006SS-2">2</A> Kouznetsov V. Palma A. Ewert C. Varlamov A. J. Heterocycl. Chem. 1998, 35: 761

Reviews:

<A NAME="RZ19006SS-3A">3a</A> Povarov LS. Russ. Chem. Rev. 1967, 36: 656

<A NAME="RZ19006SS-3B">3b</A> Boger DL. Weinreb SM. Hetero Diels-Alder Methodology in Organic Synthesis Academic Press; San Diego: 1987.

<A NAME="RZ19006SS-3C">3c</A> Weinreb SM. Comprehensive Organic Synthesis Vol. 5: Trost BM. Fleming I. Pergmon; Oxford: 1991. p.401

For recent publications, see:

<A NAME="RZ19006SS-4A">4a</A> Crousse B. Bégué J.-P. Bonnet-Delpon D. J. Org. Chem. 2000, 65: 5009

<A NAME="RZ19006SS-4B">4b</A> Laurent-Robert H. Garrigues B. Dubac J. Synlett 2000, 1160

<A NAME="RZ19006SS-4C">4c</A> Babu G. Nagarajan R. Natajan R. Perumal PT. Synthesis 2000, 661

<A NAME="RZ19006SS-4D">4d</A> Subba Reddy BV. Srinivas R. Yadav JS. Ramalingam T. Synth. Commun. 2001, 31: 1075

<A NAME="RZ19006SS-4E">4e</A> Akiyama T. Suzuki M. Kagoshima H. Heterocycles 2000, 52: 529

<A NAME="RZ19006SS-4F">4f</A> Sundararajan G. Prabagaran N. Varghese B. Org. Lett. 2001, 3: 1973

<A NAME="RZ19006SS-4G">4g</A> Spanedda MV. Hoang VD. Crousse B. Bonnet-Delpon D. Bégué J.-P. Tetrahedron Lett. 2003, 44: 217

<A NAME="RZ19006SS-4H">4h</A> Fadel F. Titouani LS. Soufiaoui M. Ajamay H. Mazzah A. Tetrahedron Lett. 2004, 45: 5905

<A NAME="RZ19006SS-5A">5a</A> Kobayashi S. Nagayama S. J. Am. Chem. Soc. 1996, 118: 8977

<A NAME="RZ19006SS-5B">5b</A> Mellor JM. Merriman GD. Tetrahedron 1995, 51: 6115

<A NAME="RZ19006SS-6A">6a</A> Kiselyov AS. Armstrong RW. Tetrahedron Lett. 1997, 38: 6163

<A NAME="RZ19006SS-6B">6b</A> Kiselyov AS. Smith L. Armstrong RW. Tetrahedron 1998, 54: 5089

<A NAME="RZ19006SS-6C">6c</A> Kiselyov AS. Smith L. Virgilio A. Armstrong RW. Tetrahedron 1998, 54: 7987

<A NAME="RZ19006SS-6D">6d</A> Ma Y. Qian C. Xie M. Sun J. J. Org. Chem. 1999, 64: 6462

<A NAME="RZ19006SS-6E">6e</A> Jones W. Kiselyov AS. Tetrahedron Lett. 2000, 41: 2309

<A NAME="RZ19006SS-6F">6f</A> Yadav JS. Reddy BVS. Madhuri C. Sabitha G. Synthesis 2001, 1065

<A NAME="RZ19006SS-6G">6g</A> Annuziata R. Benaglia M. Cinquini M. Cozzi F. Eur. J. Org. Chem. 2002, 1184

<A NAME="RZ19006SS-6H">6h</A> Ravindranath N. Ramesh C. Reddy R. Das B. Chem. Lett. 2003, 32: 222

<A NAME="RZ19006SS-6I">6i</A> Nagarajan R. Magesh CJ. Perumal PT. Synthesis 2004, 69

<A NAME="RZ19006SS-7A">7a</A> Katritzky A. Rachwak B. Rachwal S. J. Org. Chem. 1995, 60: 3993

<A NAME="RZ19006SS-7B">7b</A> Talukdar S. Chen C.-T. Fang J.-M. J. Org. Chem. 2000, 65: 3148

<A NAME="RZ19006SS-8A">8a</A> Xia C. Heng L. Ma D. Tetrahedron Lett. 2002, 43: 9405

<A NAME="RZ19006SS-8B">8b</A> Nieuwenhuyzen M. Osborne D. Stevenson PJ. Thompson N. Tetrahedron Lett. 2001, 42: 6417

<A NAME="RZ19006SS-8C">8c</A> Hadden M. Stevenson PJ. Tetrahedron Lett. 1999, 40: 1215

<A NAME="RZ19006SS-8D">8d</A> Batey RA. Simoncic PD. Lin D. Smyj RP. Lough AJ. Chem. Commun. 1999, 651

<A NAME="RZ19006SS-8E">8e</A> Batey RA. Powell DA. Acton A. Lough AJ. Tetrahedron Lett. 2001, 42: 7935

<A NAME="RZ19006SS-9">9</A> Leeson PD. Carling RW. Moore KW. Moseley AM. Smith JD. Stevenson G. Chan T. Baker R. Foster AC. Grimwood S. Kemp JA. Marshall GR. Hoogsteen K. J. Med. Chem. 1992, 35: 1964

<A NAME="RZ19006SS-10A">10a</A> Kappe CO. Munphree SS. Radwa A. Tetrahedron 1997, 53: 14179

<A NAME="RZ19006SS-10B">10b</A> Paulvannan K. Jacobs JW. Tetrahedron 1999, 55: 7433

<A NAME="RZ19006SS-10C">10c</A> Paulvannan K. Chen T. Jacobs JW. Synlett 1999, 1609

<A NAME="RZ19006SS-10D">10d</A> Ghelfi F. Parsons AF. Tommasini D. Mucci A. Eur. J. Org. Chem. 2001, 1845

<A NAME="RZ19006SS-10E">10e</A> Pedrosa F. Andrés C. Nieto J. J. Org. Chem. 2000, 65: 831

<A NAME="RZ19006SS-10F">10f</A> Paulvannan K. Hake R. Mesis R. Chen T. Tetrahedron Lett. 2002, 43: 203

<A NAME="RZ19006SS-11A">11a</A> Kametani T. Takeda H. Suzuki Y. Rasai R. Honda T. Heterocycles 1986, 24: 3385

<A NAME="RZ19006SS-11B">11b</A> Savitha G. Perumal PT. Tetrahedron Lett. 2006, 47: 3589

<A NAME="RZ19006SS-12">12</A> Puentes Ochoa C. Kouznetsov VV. J. Heterocycl. Chem. 2002, 39: 595

<A NAME="RZ19006SS-13A">13a</A> Ishihara Y. Kiyota Y. Goto G. Chem. Pharm. Bull. 1990, 38: 3024

<A NAME="RZ19006SS-13B">13b</A> Sui Z. Altom J. Nguyen VN. Fernandez J. Bernstein JI. Hiliard JJ. Barrett JF. Podlogar BL. Ohemeng KA. Bioorg. Med. Chem. 1998, 6: 735

<A NAME="RZ19006SS-14">14</A> Kouznetsov VV. Zubkov FI. Mora Cruz U. Voskressensky LG. Vargas Méndez LY. Astudillo L. Stashenko EE. Lett. Org. Chem. 2004, 1: 37

<A NAME="RZ19006SS-15">15</A> Epsztajn J. Józwiak A. Koluda P. Sadokierska I. Wilkowska ID. Tetrahedron 2000, 56: 4837

<A NAME="RZ19006SS-16">16</A> Pigeon P. Othman M. Netchitailo P. Decroix B. J. Heterocycl. Chem. 1999, 36: 691

<A NAME="RZ19006SS-17A">17a</A> Sugasawa S. Kodama K. J. Pharm. Soc. Jpn. 1942, 62: 367

<A NAME="RZ19006SS-17B">17b</A> de Diesbach H. Rey-Bellet G. Kiang TSh. Helv. Chim. Acta 1943, 26: 1869

<A NAME="RZ19006SS-18A">18a</A> Varlamov AV. Zubkov FI. Boltukhina EV. Sidorenko NV. Borisov RS. Tetrahedron Lett. 2003, 44: 3691

<A NAME="RZ19006SS-18B">18b</A> Boltukhina EV. Zubkov FI. Nikitina EV. Varlamov AV. Synthesis 2005, 1859

Crystallographic data for 6e: C₂₀H₁₉BrN₂O₃, M = 415.28, crystal dimensions: 0.15 × 0.30 × 0.50 mm, light brown prisms, T = 293 K, space group Pc, monoclinic, a = 15.442 (1), b = 20.563 (4), c = 7.855 (2) Å, α = 90.00(3)°, Z = 2, V = 879.0(3) Å³; ρ_calcd = 1.569 g/cm^-3, µ(Mo-Kα) = 2.36 cm^-1. The final R ₁ value are 0.0805 (w R ₂ ₍F²) = 0.2061) for 1244 independent reflection with I > 2σI (collected/independent reflections 3917/2230 (R _int = 0.0644)), GOOF = 0.999. Full crystallographic data for structure 6 have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication numbers CCDC 256968. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk.

All calculations were carried out with the use of the program for scaling and correction of area detector data:

<A NAME="RZ19006SS-20A">20a</A> Sheldrick GM. SADABS University of Gottingen; Germany: 1997.

Based on the method of:

<A NAME="RZ19006SS-20B">20b</A> Blessing RH. Acta Crystallogr., Sect. A 1995, 51: 33

Program for the refinement of crystal structures:

<A NAME="RZ19006SS-20C">20c</A> Sheldrick GM. SHELXL-97 University of Göttingen; Germany: 1997.

Program for the solution of crystal structures:

<A NAME="RZ19006SS-20D">20d</A> Sheldrick GM. SHELXS-97 University of Göttingen; Germany: 1997.

<A NAME="RZ19006SS-21">21</A> Pratt CS. Coyle BA. Ibers JA. J. Chem. Soc. 1971, 2146