Synthesis 2018; 50(09): 1926-1934
DOI: 10.1055/s-0036-1591896
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Approach to 5-Carboxy-1,2,3-triazoles Based on Palladium-Catalyzed Carbonylation

Yury N. Kotovshchikov
Chemistry Department, M. V. Lomonosov Moscow State University, 1/3 Leninskiye Gory, Moscow 119991, Russian Federation   Email: latyshev@org.chem.msu.ru
,
Gennadij V. Latyshev*
Chemistry Department, M. V. Lomonosov Moscow State University, 1/3 Leninskiye Gory, Moscow 119991, Russian Federation   Email: latyshev@org.chem.msu.ru
,
Irina P. Beletskaya
Chemistry Department, M. V. Lomonosov Moscow State University, 1/3 Leninskiye Gory, Moscow 119991, Russian Federation   Email: latyshev@org.chem.msu.ru
,
Nikolay V. Lukashev
Chemistry Department, M. V. Lomonosov Moscow State University, 1/3 Leninskiye Gory, Moscow 119991, Russian Federation   Email: latyshev@org.chem.msu.ru
› Author Affiliations
This work was supported by the Russian Foundation for Basic Research (grant number 16-33-00801-mol_a) and M. V. Lomonosov Moscow State University Program of Development. I. P. Beletskaya is grateful to the Russian Science Foundation (grant number 14-23-00186).
Further Information

Publication History

Received: 27 October 2017

Accepted after revision: 26 December 2017

Publication Date:
31 January 2018 (online)


Abstract

A regioselective two-step approach to 5-carboxy-1,2,3-triazoles based on palladium-catalyzed carbonylation has been developed. The protocol utilizes readily available 5-iodotriazoles as starting materials. The obtained products were used in the syntheses of fused heterocycles as well as derivatization of the steroidal hormone cortexolone­.

Supporting Information

 
  • References

    • 1a Moses JE. Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
    • 1b Franc G. Kakkar A. Chem. Commun. 2008; 5267
    • 1c Meldal M. Tornøe CW. Chem. Rev. 2008; 108: 2952
    • 1d Struthers H. Mindt TL. Schibli R. Dalton Trans. 2010; 39: 675
    • 1e Hein JE. Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
    • 1f Liang L. Astruc D. Coord. Chem. Rev. 2011; 255: 2933
    • 1g Kacprzak K. Skiera I. Piasecka M. Paryzek Z. Chem. Rev. 2016; 116: 5689
    • 1h Lau YH. Rutledge PJ. Watkinson M. Todd MH. Chem. Soc. Rev. 2011; 40: 2848
    • 1i Tiwari VK. Mishra BB. Mishra KB. Mishra N. Singh AS. Chen X. Chem. Rev. 2016; 116: 3086
    • 2a Dheer D. Singh V. Shankar R. Bioorg. Chem. 2017; 71: 30
    • 2b Thirumurugan P. Matosiuk D. Jozwiak K. Chem. Rev. 2013; 113: 4905
    • 2c Amblard F. Cho JH. Schinazi RF. Chem. Rev. 2009; 109: 4207
    • 2d Agalave SG. Maujan SR. Pore VS. Chem. Asian J. 2011; 6: 2696
    • 3a Cheng H. Wan J. Lin M.-I. Liu Y. Lu X. Liu J. Xu Y. Chen J. Tu Z. Cheng Y.-SE. Ding K. J. Med. Chem. 2012; 55: 2144
    • 3b Komsani JR. Avula S. Koppireddi S. Koochana PK. USN M. Yadla R. J. Heterocycl. Chem. 2015; 52: 764
    • 3c Gadaginamath GS. Bhovi MG. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2005; 44: 1068
    • 3d Akritopoulou-Zanze I. Wakefield BD. Mack H. Turner SC. Gasiecki AF. Gracias VJ. Sarris K. Kalvin DM. Michmerhuizen MJ. Shuai Q. Patel JR. Bakker M. Teusch N. Johnson ET. Kovar PJ. Djuric SW. Long AJ. Vasudevan A. Hobson A. Nigel St JM. Wang L. George D. Li B. Frank K. (Abbot Laboratories) PCT Int. Appl. WO2008/154241 A1, 2008
    • 3e Budzik BW. Evans KA. Wisnoski DD. Jin J. Rivero RA. Szewczyk R. Jayawickreme C. Moncol DL. Yu H. Bioorg. Med. Chem. Lett. 2010; 20: 1363
    • 3f Zhang H. Ryono DE. Devasthale P. Wang W. O’Malley K. Farrelly D. Gu L. Harrity T. Cap M. Chu C. Locke K. Zhang L. Lippy J. Kunselman L. Morgan N. Flynn N. Moore L. Hosagrahara V. Zhang L. Kadiyala P. Xu C. Doweyko AM. Bell A. Chang C. Muckelbauer J. Zahler R. Hariharan N. Cheng PT. W. Bioorg. Med. Chem. Lett. 2009; 19: 1451
    • 3g Bode CM. Boezio AA. Albrecht BK. Bellon F. Berry L. Broome MA. Choquette D. Dussault I. Lewis RT. Lin M.-HJ. Rex K. Whittington DA. Yang Y. Harmange J.-C. Bioorg. Med. Chem. Lett. 2012; 22: 4089
    • 3h Futatsugi K. Bahnck KB. Brenner MB. Buxton J. Chin JE. Coffey SB. Dubins J. Flynn D. Gautreau D. Guzman-Perez A. Hadcock JR. Hepworth D. Herr M. Hinchey T. Janssen AM. Jennings SM. Jiao W. Lavergne SY. Li B. Li M. Munchhof MJ. Orr ST. M. Piotrowski DW. Roush NS. Sammons M. Stevens BD. Storer G. Wang J. Warmus JS. Wei L. Wolford AC. Med. Chem. Commun. 2013; 4: 205
    • 4a Youcef RA. Dos Santos M. Roussel S. Baltaze J.-P. Lubin-Germain N. Uziel J. J. Org. Chem. 2009; 74: 4318
    • 4b Grée D. Grée R. Tetrahedron Lett. 2007; 48: 5435
    • 4c Earl RA. Townsend LB. Can. J. Chem. 1980; 58: 2550
    • 4d L’Abbe G. Dehaen W. Tetrahedron 1988; 44: 461
    • 4e Smalley TL. Jr. Boggs S. Caravella JA. Chen L. Creech KL. Deaton DN. Kaldor I. Parks DJ. Bioorg. Med. Chem. Lett. 2015; 25: 280
    • 4f Ostrowski T. Januszczyk P. Cieslak M. Kazmierczak-Baranska J. Nawrot B. Bartoszak-Adamska E. Zeidler J. Bioorg. Med. Chem. 2011; 19: 4386
    • 4g Qian Y. Hamilton M. Sidduri A. Gabriel S. Ren Y. Peng R. Kondru R. Narayanan A. Truitt T. Hamid R. Chen Y. Zhang L. Fretland AJ. Sanchez RA. Chang K.-C. Lucas M. Schoenfeld RC. Laine D. Fuentes ME. Stevenson CS. Budd DC. J. Med. Chem. 2012; 55: 7920
    • 5a Hein JE. Tripp JC. Krasnova LB. Sharpless KB. Fokin VV. Angew. Chem. Int. Ed. 2009; 48: 8018
    • 5b Smith NW. Polenz BP. Johnson SB. Dzyuba SV. Tetrahedron Lett. 2010; 51: 550
    • 5c Li L. Hao G. Zhu A. Liu S. Zhang G. Tetrahedron Lett. 2013; 54: 6057
    • 5d García-Álvarez J. Díez J. Gimeno J. Green Chem. 2010; 12: 2127
    • 5e García-Álvarez J. Díez J. Gimeno J. Suárez FJ. Vincent C. Eur. J. Inorg. Chem. 2012; 5854
    • 5f Lal S. Rzepa HS. Díez-González S. ACS Catal. 2014; 4: 2274
    • 5g Brotherton WS. Clark RJ. Zhu L. J. Org. Chem. 2012; 77: 6443
    • 5h Li L. Zhang G. Zhu A. Zhang L. J. Org. Chem. 2008; 73: 3630
    • 5i Barsoum DN. Brassard CJ. Deeb JH. A. Okashah N. Sreenath K. Simmons JT. Zhu L. Synthesis 2013; 45: 2372
    • 5j Vidal C. García-Álvarez J. Green Chem. 2014; 16: 3515
    • 5k Li L. Li Y. Li R. Zhu A. Zhang G. Aust. J. Chem. 2011; 64: 1383
    • 5l Li L. Ding S. Yang Y. Zhu A. Fan X. Cui M. Chen C. Zhang G. Chem. Eur. J. 2017; 23: 1166
    • 6a Testa A. Piras M. Hickey MJ. Fleming IN. Bushby N. Lenz E. Elmore CS. Zanda M. Synlett 2014; 25: 1019
    • 6b Carcenac Y. David-Quillot F. Abarbri M. Duchêne A. Thibonnet J. Synthesis 2013; 45: 633
    • 6c Bogdan AR. James K. Org. Lett. 2011; 13: 4060
    • 6d Juríček M. Stout K. Kouwer PH. J. Rowan AE. Org. Lett. 2011; 13: 3494
    • 6e Dinér P. Andersson T. Kjellén J. Elbing K. Hohmann S. Grøtli M. New J. Chem. 2009; 33: 1010
    • 6f Schulman JM. Friedman AA. Panteleev J. Lautens M. Chem. Commun. 2012; 48: 55
    • 6g Deng J. Wu Y.-M. Chen Q.-Y. Synthesis 2005; 2730
    • 6h Fehér K. Gömöry Á. Skoda-Földes R. Monatsh. Chem. 2015; 146: 1455
    • 6i Li L. Shang T. Ma X. Guo H. Zhu A. Zhang G. Synlett 2015; 26: 695
    • 7a Skoda-Földes R. Kollár L. Curr. Org. Chem. 2002; 6: 1097
    • 7b Brennführer A. Neumann H. Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
    • 7c Gadgea ST. Bhanage BM. RSC Adv. 2014; 4: 10367
    • 7d Wu X.-F. Neumann H. Beller M. Chem. Rev. 2013; 113: 1
    • 7e Barnard CF. J. Organometallics 2008; 27: 5402
    • 7f Fang W. Zhu H. Deng Q. Liu S. Liu X. Shen Y. Tu T. Synthesis 2014; 46: 1689
    • 7g Bai Y. Davis DC. Dai M. J. Org. Chem. 2017; 82: 2319
  • 8 Beller M. Mägerlein W. Indolese AF. Fischer C. Synthesis 2001; 1098
    • 9a Reetz MT. Westermann E. Angew. Chem. Int. Ed. 2000; 39: 165
    • 9b Ananikov VP. Beletskaya IP. Organometallics 2012; 31: 1595
    • 9c Beletskaya I. Tyurin V. Molecules 2010; 15: 4792
    • 9d Beletskaya IP. Khokhlov AR. Tarasenko EA. Tyurin VS. J. Organomet. Chem. 2007; 692: 4402
    • 9e Sigeev AS. Peregudov AS. Cheprakov AV. Beletskaya IP. Adv. Synth. Catal. 2015; 357: 417
    • 9f Kashin AN. Ganina OG. Cheprakov AV. Beletskaya IP. ChemCatChem 2015; 7: 2113
  • 10 Chandrappa S. Vinaya K. Ramakrishnappa T. Rangappa KS. Synlett 2010; 3019
  • 11 Irastorza A. Aizpurua JM. Correa A. Org. Lett. 2016; 18: 1080
  • 12 Kotovshchikov YN. Latyshev GV. Lukashev NV. Beletskaya IP. Org. Biomol. Chem. 2014; 12: 3707
  • 13 Zhou Y. Lecourt T. Micouin L. Angew. Chem. Int. Ed. 2010; 49: 2607