A Comprehensive Study of the
Heterocyclizations of N-Arylmaleimides
and 6-Aminouracils

Roman V. Rudenko; Sergey A. Komykhov; Sergey M. Desenko; Yulia V. Sen’ko; Oleg V. Shishkin; Irina S. Konovalova; Svetlana V. Shishkina; Valentin A. Chebanov

doi:10.1055/s-0030-1260163

PAPER

A Comprehensive Study of the Heterocyclizations of N-Arylmaleimides and 6-Aminouracils

Roman V. Rudenko^a, Sergey A. Komykhov*^a, Sergey M. Desenko^a,b, Yulia V. Sen’ko^a, Oleg V. Shishkin^a,b, Irina S. Konovalova^a, Svetlana V. Shishkina^a, Valentin A. Chebanov*^a
^a State Scientific Institution, ‘Institute for Single Crystals’ of National Academy of Sciences of Ukraine, Lenin Ave. 60, 61001 Kharkiv, Ukraine
Fax: +38(57)3410273; e-Mail: komykhov@isc.kharkov.com; e-Mail: chebanov@isc.kharkov.com;
^b Karazin Kharkiv National University, Svobody sq. 4, 61077 Kharkiv, Ukraine

Abstract

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Abstract

Heterocyclization reactions between N-arylmaleimides and 6-aminouracils were studied in detail. It was established that several directions are possible depending on the nature of reaction medium and the substituent character in the uracil component. The synthetic procedure leading to N-phenyl-2,4,7-trioxopyrido[2,3-d]pyrimidine-5-carboxamides in good-to-high yields was developed and key stages of the corresponding reaction were established.

Key words

heterocycles - nucleophilic addition - ring opening - pyridines - pyrroles - annulation - regioselectivity

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References

See, for example:

<A NAME="RT56611SS-1A">1a</A> Alajarin R. Avarez-Buila J. Vaquero JJ. Sunkel C. Fau J. Statkov P. Sanz J. Tetrahedron: Asymmetry 1993, 4: 617

<A NAME="RT56611SS-1B">1b</A> Bossert F. Vater W. Med. Res. Rev. 1989, 9: 291

<A NAME="RT56611SS-1C">1c</A> Trigle DJ. Langs DA. Janis RA. Med. Res. Rev. 1989, 9: 123

<A NAME="RT56611SS-1D">1d</A> Tsuda Y, Mishina T, Obata M, Araki K, Inui J, and Nakamura T. inventors; Patent WO 8504172. ; Chem. Abstr. 1986, 104, 207298

<A NAME="RT56611SS-1E">1e</A> Tsuda Y, Mishina T, Obata M, Araki K, Inui J, and Nakamura T. inventors; Japanese Patent JP 61227584. ; Chem. Abstr. 1988, 109, 120988

<A NAME="RT56611SS-1F">1f</A> Tsuda Y, Mishina T, Obata M, Araki K, Inui J, and Nakamura T. inventors; European Patent EP 0217142. ; Chem. Abstr. 1987, 106, 213976

<A NAME="RT56611SS-1G">1g</A> Atwal KS, Vaccaro W, Lloyd J, Finlay H, Yan L, and Bhandaru RS. inventors; Patent WO 0140231. ; Chem. Abstr. 2003, 135, 19660

<A NAME="RT56611SS-1H">1h</A> Atwal KS. Moreland S. Bioorg. Med. Chem. Lett. 1991, 1: 291

<A NAME="RT56611SS-1I">1i</A> Kappe CO. Eur. J. Med. Chem. 2000, 35: 1043

<A NAME="RT56611SS-1J">1j</A> Ram VJ. Goel A. Sarkhel S. Maulik PR. Bioorg. Med. Chem. 2002, 10: 1275

<A NAME="RT56611SS-1K">1k</A> Tenser RB. Gaydos A. Hay KA. Antimicrob. Agents Chemother. 2001, 45: 3657

<A NAME="RT56611SS-1L">1l</A> Gready JE. McKinlay C. Gebauer MG. Eur. J. Med. Chem. 2003, 38: 719

See, for example:

<A NAME="RT56611SS-2A">2a</A> Quiroga J. Insuasty B. Sanchez A. J. Heterocycl. Chem. 1992, 29: 1045

<A NAME="RT56611SS-2B">2b</A> Rodrigues R. Suarez M. Ochoa E. J. Heterocycl. Chem. 1996, 33: 45

<A NAME="RT56611SS-2C">2c</A> Powers DG. Casebier DS. Fokas D. Tetrahedron 1998, 54: 4085

<A NAME="RT56611SS-2D">2d</A> Takahashi M. Nagaoka H. Inoue K. J. Heterocycl. Chem. 2004, 41: 525

<A NAME="RT56611SS-2E">2e</A> Chebanov VA. Saraev VE. Gura EA. Desenko SM. Musatov VI. Collect. Czech. Chem. Commun. 2005, 70: 350

<A NAME="RT56611SS-2F">2f</A> Hassan NA. Hegab MI. Hashem AI. J. Heterocycl. Chem. 2007, 44: 775

<A NAME="RT56611SS-2G">2g</A> Shi D.-Q. Ni S.-N. Yang F. J. Heterocycl. Chem. 2008, 45: 693

<A NAME="RT56611SS-2H">2h</A> Shi D.-Q. Niu L.-H. Yao H. J. Heterocycl. Chem. 2009, 46: 237

<A NAME="RT56611SS-3A">3a</A> Marrian DH. J. Chem. Soc. 1949, 1797

<A NAME="RT56611SS-3B">3b</A> Augustin M. Rudorf W.-D. Pasche R. Z. Chem. 1974, 14: 434

<A NAME="RT56611SS-3C">3c</A> Shimo T. Matsuda Y. Iwanaga T. Shinmyozu T. Somekawa K. Heterocycles 2007, 71: 1053

<A NAME="RT56611SS-3D">3d</A> Havrylyuk D. Zimenkovsky B. Lesyk R. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184: 638

<A NAME="RT56611SS-3E">3e</A> Rudenko RV. Komykhov SA. Desenko SM. Chem. Heterocycl. Compd. 2009, 45: 1017

<A NAME="RT56611SS-4">4</A> Augustin M. Mueller W. J. Prakt. Chem. 1985, 327: 789

<A NAME="RT56611SS-5">5</A> Ito I. Oda N. Kato T. Chem. Pharm. Bull. 1976, 24: 1189

<A NAME="RT56611SS-6">6</A> Abelman MM. Fisher KJ. Doerffler E. Edwards PJ. Tetrahedron Lett. 2003, 44: 1823

<A NAME="RT56611SS-7">7</A> Lesyk R. Vladzimirska O. Holota S. Zaprutko L. Gzella A. Eur. J. Med. Chem. 2007, 42: 641

<A NAME="RT56611SS-8">8</A> Shah KR. Blanton CD. J. Org. Chem. 1982, 47: 502

<A NAME="RT56611SS-9">9</A> Cobo J. Sánchez A. Nogueras M. Tetrahedron 1998, 54: 5753

<A NAME="RT56611SS-10A">10a</A> Velchinskaya E. Kuz’menko I. Kulik L. Pharm. Chem. J. 1999, 33: 155

<A NAME="RT56611SS-10B">10b</A> Velchinskaya E. Petsushak B. Rogal A. Chem. Heterocycl. Compd. 2007, 43: 695

<A NAME="RT56611SS-11">11</A> Rudenko RV. Komykhov SA. Musatov VI. Konovalova IS. Shishkin OV. Desenko SM.
J. Heterocycl. Chem. 2011, 48: 888

<A NAME="RT56611SS-12">12</A> Rudenko RV. Komykhov SA. Desenko SM. Musatov VI. Shishkin OV. Konovalova IS. Vashchenko EV. Chebanov VA. Synthesis 2011, 783

<A NAME="RT56611SS-13">13</A> Shishkin OV. Russ. Chem. Bull. 1997, 46: 1510

<A NAME="RT56611SS-14A">14a</A> Shishkin OV. Gorb L. Hobza P. Leszczynski J. Int. J. Quantum Chem. 2000, 80: 1116

<A NAME="RT56611SS-14B">14b</A> Isayev O. Furmanchuk A. Shishkin OV. Gorb L. Leszczynski J. J. Phys. Chem. B. 2007, 111: 3476

The final atomic coordinates and crystallographic data for molecule 3j have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk] and are available on request quoting the deposition number CCDC 824124.

<A NAME="RT56611SS-16">16</A> Sheldrick GM. Acta Crystallogr., Sect. A 2008, 64: 112