Synthesis of 6-Amino-2-bromo-4-hydroxynicotinaldehyde
Derivatives

Alexander V. Denisenko; Anton V. Tverdokhlebov; Andrey A. Tolmachev; Yulian M. Volovenko; Svitlana V. Shishkina; Oleg V. Shishkin

doi:10.1055/s-0030-1258371

PAPER

Synthesis of 6-Amino-2-bromo-4-hydroxynicotinaldehyde Derivatives

Alexander V. Denisenko^a, Anton V. Tverdokhlebov*^b, Andrey A. Tolmachev^a,b, Yulian M. Volovenko^a, Svitlana V. Shishkina^c, Oleg V. Shishkin^c
^a Kiev National Taras Shevchenko University, Volodimirska str., 62, 01033 Kiev, Ukraine
^b Enamine Ltd., Alexandra Matrosova str., 23, 01103 Kiev, Ukraine
Fax: +380445373253; e-Mail: atver@univ.kiev.ua;
^c STC Institute for Single Crystals, NAS of Ukraine, 60 Lenina ave., 61001 Kharkiv, Ukraine

Abstract

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Abstract

Acylation of (1,3-dimethylbenzimidazol-2-ylidene)-, (3-methylbenzothiazol-2-ylidene)-, and (3,4-dimethylthiazol-2-ylidene)-acetonitriles with 1-(cyanoacetyl)-3,5-dimethylpyrazole was found to proceed at the exocyclic carbon atom, yielding the appropriate 2-heterylidene-3-oxopentanedinitriles. Treatment of the prepared dinitriles with hydrobromic acid in refluxing acetic acid afforded 2-(6-amino-2-bromo-4-hydroxypyridin-3-yl)-substituted quaternary salts of benzimidazolium, benzothiazolium, and thiazolium. Their structures were confirmed unambiguously by X-ray crystallographic studies. Reduction of these quaternary salts with excess sodium borohydride yielded the corresponding dihydro (in the case of benzoazoles) or tetrahydro (in the case of thiazole) derivatives, which were shown to be synthetic equivalents of the title nicotinaldehyde.

Key words

aldehydes - heterocycles - hydrazones - nitriles - pyridines

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References

<A NAME="RP16110SS-1A">1a</A> Tran JA. Jiang W. Tucci FC. Fleck BA. Wen J. Sai Y. Madan A. Chen TK. Markison S. Foster AC. Hoare SR. Marks D. Harman J. Chen CW. Arellano M. Marinkovic D. Bozigian H. Sanders J. Chen C. J. Med. Chem. 2007, 50: 6356

<A NAME="RP16110SS-1B">1b</A> Wang X. Snieckus V. Tetrahedron Lett. 1991, 32: 4883

<A NAME="RP16110SS-1C">1c</A> Harrowven DC. Tetrahedron Lett. 1993, 34: 5653

<A NAME="RP16110SS-1D">1d</A> Staab HA. Diehm M. Krieger C. Tetrahedron Lett. 1994, 35: 8357

<A NAME="RP16110SS-2A">2a</A> Chelucci G. Baldino S. Pinna GA. Sechi B. Tetrahedron Lett. 2008, 46: 2839

<A NAME="RP16110SS-2B">2b</A> Robert N. Hoarau C. Celanire S. Ribereau P. Godard A. Queguiner G. Marsais F. Tetrahedron 2005, 61: 4569

<A NAME="RP16110SS-2C">2c</A> Lyaskovskyy V. Fröhlich R. Würthwein E.-U. Synthesis 2007, 2135

<A NAME="RP16110SS-2D">2d</A> Song ZJ. Zhao M. Desmond R. Devine P. Tschaen DM. Frey L. Heid R. Xu F. Foster B. Li J. Reamer R. Volante R. Grabowski EJJ. Dolling UH. Reider PJ. Okada S. Kato Y. Mano E. J. Org. Chem. 1999, 64: 9658

<A NAME="RP16110SS-2E">2e</A> Numata A. Kondo Y. Sakamoto T. Synthesis 1999, 306

<A NAME="RP16110SS-3A">3a</A> de la Fuente MC. Dominguez D. Tetrahedron 2009, 65: 3653

<A NAME="RP16110SS-3B">3b</A> Srinivasan JM. Bruks HE. Smith CR. Viswanatan R. Johnston JN. Synthesis 2005, 330

<A NAME="RP16110SS-3C">3c</A> Chelucci G. Addis D. Baldino S. Tetrahedron Lett. 2007, 48: 3359

<A NAME="RP16110SS-3D">3d</A> Kato Y. Niiyama K. Nemoto T. Jona H. Akao A. Okada S. Song ZJ. Zhao M. Tsuchiya Y. Tomimoto K. Mase T. Tetrahedron 2002, 58: 3409

<A NAME="RP16110SS-3E">3e</A> Song ZJ. Zhao M. Frey L. Li J. Tan L. Chen CY. Tschaen DM. Tillyer M. Grabowski EJJ. Volante R. Reider PJ. Org. Lett. 2001, 3: 3357

<A NAME="RP16110SS-4A">4a</A> Ilyashenko G. Choudhury R. Motevalli M. Watkinson M. Synlett 2006, 1759

<A NAME="RP16110SS-4B">4b</A> Mase T. Houpis IN. Akao A. Dorriotis I. Emerson Kh. Hoang T. Iida T. Itoh T. Kamei K. Kato S. Kato Y. Kawasaki M. Lang F. Lee J. Lynch J. Maligres P. Molina A. Nemoto T. Okada S. Reamer R. Song JZ. Tschaen D. Wada T. Zewge D. Volante RP. Reider PJ. Tomimoto K. J. Org. Chem. 2001, 66: 6775

<A NAME="RP16110SS-4C">4c</A> Bracher F. J. Heterocycl. Chem. 1993, 30: 157

<A NAME="RP16110SS-4D">4d</A> Melnyk P. Gasche J. Thal C. Synth. Commun. 1993, 23: 2727

<A NAME="RP16110SS-5A">5a</A> Mandal AB. Augustine JK. Quattropani A. Bombrun A. Tetrahedron Lett. 2005, 46: 6033

<A NAME="RP16110SS-5B">5b</A> Horn U. Mutterer F. Weis CD. Helv. Chim. Acta 1976, 59: 211

<A NAME="RP16110SS-5C">5c</A> Mutterer F. Weis CD. Helv. Chim. Acta 1976, 59: 229

<A NAME="RP16110SS-6A">6a</A> Craig JC. Ekwuribe NN. Fu CC. Walker KAM. Synthesis 1981, 303

<A NAME="RP16110SS-6B">6b</A> Ramos JM. Tarazi M. Wuest JD. J. Org. Chem. 1987, 52: 5437

<A NAME="RP16110SS-6C">6c</A> Katritzky AR. Aslan DC. Oniciu DC. Tetrahedron: Asymmetry 1998, 2245

<A NAME="RP16110SS-6D">6d</A> Lee I.-SH. Jeoung EH. Kreevoy MM. J. Am. Chem. Soc. 1997, 119: 2722

<A NAME="RP16110SS-6E">6e</A> Lee I.-SH. Jeoung EH. J. Org. Chem. 1998, 63: 7275

<A NAME="RP16110SS-7A">7a</A> Chikashita H. Ikegami S. Okumura T. Itoh K. Synthesis 1986, 375

<A NAME="RP16110SS-7B">7b</A> Chikashita H. Ishibaba M. Ori K. Itoh K. Bull. Chem. Soc. Jpn. 1988, 61: 3637

<A NAME="RP16110SS-7C">7c</A> Corey EJ. Boger DL. Tetrahedron Lett. 1978, 5

<A NAME="RP16110SS-7D">7d</A> Corey EJ. Boger DL. Tetrahedron Lett. 1978, 9

<A NAME="RP16110SS-7E">7e</A> Corey EJ. Boger DL. Tetrahedron Lett. 1978, 13

<A NAME="RP16110SS-7F">7f</A> Chikashita H. Itoh K. Heterocycles 1985, 23: 295

<A NAME="RP16110SS-8A">8a</A> Tverdokhlebov AV. Denisenko AV. Tolmachev AA. Volovenko YuM. Synthesis 2007, 1811

<A NAME="RP16110SS-8B">8b</A> Denisenko AV. Tverdokhlebov AV. Tolmachev AA. Volovenko YuM. Shishkina SV. Shishkin OV. Synthesis 2010, 1009

<A NAME="RP16110SS-8C">8c</A> Tverdokhlebov AV. Denisenko AV. Tolmachev AA. Volovenko YuM. Shishkina SV. Shishkin OV. Synthesis 2009, 1265

<A NAME="RP16110SS-9A">9a</A> Rudnev MI. Kurbatov VP. Chub NK. Osipov OA. J. Gen. Chem. USSR (Engl. Transl.) 1988, 58: 2077 ; Zh. Obshch. Khim. 1988, 58, 2334

<A NAME="RP16110SS-9B">9b</A> Van Dormael A. Nys J. Bull. Soc. Chim. Belg. 1950, 59: 588

<A NAME="RP16110SS-9C">9c</A> Doyle FP, and Kendall JD. inventors; US Patent 2542401. ; Chem. Abstr. 1951, 45, 10109

<A NAME="RP16110SS-10A">10a</A> Büttelmann B. Peters J.-U. Ceccarelli S. Kolczewski S. Vieira E. Prinssen EP. Spooren W. Schuler F. Huwyler J. Porter RHP. Jaeschke G. Bioorg. Med. Chem. Lett. 2006, 16: 1892

<A NAME="RP16110SS-10B">10b</A> Mascal M. Hext NM. Warmuth R. Arnall-Culliford JR. Moore MH. Turkenburg JP. J. Org. Chem. 1999, 64: 8479

<A NAME="RP16110SS-10C">10c</A> Carboni RA. Coffman DD. Howard EG. J. Am. Chem. Soc. 1958, 80: 2838

<A NAME="RP16110SS-11A">11a</A> Neumeyer JL. Weinhardt KK. J. Med. Chem. 1973, 16: 808

<A NAME="RP16110SS-11B">11b</A> Neumeyer JL. Weinhardt KK. J. Med. Chem. 1970, 13: 613

<A NAME="RP16110SS-11C">11c</A> Sommer MB. Begtrup M. Bøgesø KP. J. Org. Chem. 1990, 55: 4822

<A NAME="RP16110SS-11D">11d</A> Deady LW. Ganakas A.-M. Ong BH. Aust. J. Chem. 1989, 42: 1029

<A NAME="RP16110SS-11E">11e</A> Johnson F. Nasutavicus WA. J. Org. Chem. 1962, 27: 3953

<A NAME="RP16110SS-11F">11f</A> Wan Y. Niu W. Behof WJ. Wang Y. Boyle P. Gorman CB. Tetrahedron 2009, 65: 4293

<A NAME="RP16110SS-11G">11g</A> Frohn M. Bürli RW. Riahi B. Hungate RW. Tetrahedron Lett. 2007, 48: 487

<A NAME="RP16110SS-12A">12a</A> Koitz G. Thierrichter B. Junek H. Heterocycles 1983, 20: 2405

<A NAME="RP16110SS-12B">12b</A> Victory PJ. Teixido J. Borrell JI. Busquets N. Heterocycles 1993, 36: 1

<A NAME="RP16110SS-12C">12c</A> Victory PJ. Teixido J. Borrell JI. Heterocycles 1992, 34: 1905

<A NAME="RP16110SS-12D">12d</A> Hersperger R. Bray-French K. Mazzoni L. Müller T. J. Med. Chem. 2000, 43: 675

<A NAME="RP16110SS-12E">12e</A> Teixido J. Borrell JI. Serra B. Matallana JL. Colominas C. Carrion F. Pascual R. Falco JL. Batllori X. Heterocycles 1999, 50: 739

<A NAME="RP16110SS-12F">12f</A> Victory P. Busquets N. Borrell JI. Teixido J. Serra B. Matallana JL. Junek H. Sterk H. Heterocycles 1995, 41: 1013

<A NAME="RP16110SS-13">13</A> Ried W. Meyer A. Chem. Ber. 1957, 90: 2841

<A NAME="RP16110SS-14A">14a</A> Ried W. Schleimer B. Angew. Chem. 1958, 70: 164

<A NAME="RP16110SS-14B">14b</A> Gorobets NYu. Yousefi BH. Belaj F. Kappe CO. Tetrahedron 2004, 60: 8633

<A NAME="RP16110SS-14C">14c</A> Stetinova J. Kada R. Lesko J. Zalibera L. Ilavsky D. Bartovic A. Collect. Czech. Chem. Commun. 1995, 60: 999

<A NAME="RP16110SS-14D">14d</A> Stetinova J. Kada R. Lesko J. Dandarova M. Krublova M. Collect. Czech. Chem. Commun. 1996, 61: 921

<A NAME="RP16110SS-14E">14e</A> Ried W. Schleimer B. Justus Liebigs Ann. Chem. 1959, 626: 98

<A NAME="RP16110SS-14F">14f</A> Ried W. Köcher EU. Justus Liebigs Ann. Chem. 1961, 647: 116

<A NAME="RP16110SS-14G">14g</A> Ried W. Schubert HJ. Justus Liebigs Ann. Chem. 1962, 653: 181

<A NAME="RP16110SS-14H">14h</A> Ried W. Schleimer B. Justus Liebigs Ann. Chem. 1959, 626: 106

<A NAME="RP16110SS-14I">14i</A> Jahine H. Zaher HA. Sayed A. Seada M. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1977, 15: 352

<A NAME="RP16110SS-14J">14j</A> Stetinova J. Kada R. Lesko J. Molecules 1996, 1: 251

<A NAME="RP16110SS-14K">14k</A> Stetinova J. Kada R. Dandarova M. Krublova M. Lesko J. Chem. Heterocycl. Compd. (Engl. Transl.) 1995, 31: 1231

<A NAME="RP16110SS-15A">15a</A> Zakhs ER. Ponyaev AI. Subbotina MA. El’tsov AV. Russ. J. Gen. Chem. (Engl. Transl.) 2001, 71: 1076 ; Zh. Obshch. Khim. 2001, 71, 1142

<A NAME="RP16110SS-15B">15b</A> Yagupolski LM. Kulchitsky MM. Ilchenko AYa. J. Org. Chem. USSR (Engl. Transl.) 1974, 10: 1326 ; Zh. Org. Khim. 1974, 10, 1321

<A NAME="RP16110SS-15C">15c</A> Zakhs ER. Subbotina MA. El’tsov AV. J. Org. Chem. USSR (Engl. Transl.) 1979, 15: 178 ; Zh. Org. Khim. 1979, 15, 200

<A NAME="RP16110SS-16A">16a</A> Zhang MQ. Haemers A. van den Berghe D. Pattyn SR. Bollaert W. Levshin I. J. Heterocycl. Chem. 1991, 28: 685

<A NAME="RP16110SS-16B">16b</A> Clarke GM. Sykes P. J. Chem. Soc. C 1967, 1269

<A NAME="RP16110SS-17">17</A> Menta E, Da Re G, and Grugni M. inventors; WO 2003105842.

<A NAME="RP16110SS-18">18</A> Scheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64: 112