PDF icon PDF herunterladen
Open Access
CC BY-NC-ND 4.0 · SynOpen 2022; 06(02): 132-140
DOI: 10.1055/s-0041-1737605
paper

Microwave-Assisted, Metal-Free, Chemoselective N-Formylation of Amines using 2-Formyl-1,3-dimethyl-1H-imidazol-3-ium Iodide and In Situ Synthesis of Benzimidazole and Isocyanides

Gullahalli S. Jagadeesha
a   Government S K S J Technological Institute, Affiliated to Visvesvaraya Technological University, K R Circle, Bangalore-560001, Karnataka, India
,
Kempegowda Mantelingu 
b   Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570006, Karnataka, India
,
Naraganahalli R. Thimmegowda  ∗
a   Government S K S J Technological Institute, Affiliated to Visvesvaraya Technological University, K R Circle, Bangalore-560001, Karnataka, India
,
Kanchugarakoppal S. Rangappa∗
c   Institution of Excellence, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
› Institutsangaben
Financial support from the Vision Group on Science and Technology, Government of Karnataka (No. VGST/SMYSR/GRD-426) is gratefully acknowledged.
› Weitere Informationen
  Lizenzen und Reprints Alle Artikel dieser Rubrik


Preview

Erratum zu diesem Artikel:

Microwave-Assisted, Metal-Free, Chemoselective N-Formylation of Amines using 2-Formyl-1,3-dimethyl-1H-imidazol-3-ium Iodide and In Situ Synthesis of Benzimidazole and IsocyanidesSynOpen 2022; 06(02): e1-e1
DOI: 10.1055/s-0040-1720034

Abstract

An efficient, environmentally benign, chemoselective, microwave-assisted N-formylation protocol of aromatic, aliphatic, alicyclic, benzylic amines, inactivated aromatic amines and sterically demanding heterocyclic amines using 2-formyl-1,3-dimethyl-1H-imidazol-3-ium iodide has been developed. This affords a series of N-substituted formamides with good to excellent yields (23 examples, 53–96% yield) and can be readily scaled. The methodology can be further extended to synthesize benzimidazole and isocyanide derivatives.

Key words

N -formylation - N-formamide - microwave-assisted synthesis - 2-formyl-1,3-dimethyl-1H-imidazol-3-ium iodide - isocyanide - benzimidazole

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737605. Included are the synthetic procedure for the synthesis of formylating agent 2 as well as 1H NMR, 13C NMR, LCMS, HRMS data for formylating agent 2 and final compounds 3a–p, 5a–g, 6a, 6b and 6c.
  • Supporting Information


Publikationsverlauf

Eingereicht: 20. März 2022

Angenommen nach Revision: 27. April 2022

Artikel online veröffentlicht:
08. Juni 2022

© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
    Suche in Google Scholar
  • 2 Shaw AJ, Gescher A, Mraz J. Toxicol. Appl. Pharmacol. 1988; 95: 162
    Suche in Google Scholar
  • 3 Simons C, van Leeuwen JG. E, Stemmer R, Arends IW. C. E, Maschmeyer T, Sheldon RA, Hanefeld U. J. Mol. Catal. 2008; 54: 67
    Suche in Google Scholar
  • 4 Das B, Krishnaiah M, Balasubramanyam P, Veeranjaneyulu B, Kumar DN. Tetrahedron Lett. 2008; 49: 2225
    Suche in Google Scholar
  • 5 Keita M, Vandamme M, Mahe O, Paquin JF. Tetrahedron Lett. 2015; 56: 461
    Suche in Google Scholar
  • 6 Guchhait S, Priyadarshani G, Chaudhary V, Seladiya D, Tapan S, Bhogayta N. RSC Adv. 2013; 16: 10867
    Suche in Google Scholar
  • 7 Han Y, Cai L. Tetrahedron Lett. 1977; 31: 5423
    Suche in Google Scholar
  • 8 Kobayashi S, Nishio K. J. Org. Chem. 1994; 59: 6620
    Suche in Google Scholar
  • 9 Iseki K, Mizuno S, Kuroki Y, Kobayashi Y. Tetrahedron 1999; 55: 977
    Suche in Google Scholar
  • 10 Kobayashi S, Yasuda M, Hachiya I. Chem. Lett. 1996; 25: 407
    Suche in Google Scholar
  • 11 Huang H, Lin X, Yen S, Liang C. Org. Biomol. Chem. 2020; 18: 5726
    Suche in Google Scholar
  • 12 Bucek J, Zatloukal M, Havlicek L, Plihalova L, Pospisil T, Novak O, Dolezal K, Strnad M. R. Soc. Open Sci. 2018; 5: 181322
    Suche in Google Scholar
  • 13 Saladino R, Crestini C, Ciciriello F, Costanzo G, Di Mauro E. Chem. Biodivers. 2007; 4: 694
    Suche in Google Scholar
  • 14 Blake RD, Delcourt SG. Nucleic Acids Res. 1996; 24: 2095
    Suche in Google Scholar
  • 15 Gibbons BJ, Hurley TD. Biochemistry 2004; 43: 12555
    Suche in Google Scholar
  • 16 Strazzolini P, Giumanini AG, Cauci S. Tetrahedron 1990; 46: 1081
    Suche in Google Scholar
  • 17 Kandula V, Gudipati R, Chatterjee A, Yennam S, Behera M. SynOpen 2018; 2: 176
    Suche in Google Scholar
  • 18 Waki J, Meienhofer J. J. Org. Chem. 1977; 42: 2019
    Suche in Google Scholar
  • 19 Olah GA, Ohannesian L, Arvanaghi M. Chem. Rev. 1987; 87: 671
    Suche in Google Scholar
  • 20 Preedasuriyachai P, Kitahara H, Chavasiri W, Sakurai H. Chem. Lett. 2010; 42: 1174
    Suche in Google Scholar
  • 21 Chapman RS. L, Lawrence R, Williams JM. J, Bull SD. Org. Lett. 2017; 19: 4908
    Suche in Google Scholar
  • 22 Noh HW, An Y, Lee S, Jung J, Son SU, Jang HY. Adv. Synth. Catal. 2019; 361: 3068
    Suche in Google Scholar
  • 23 Federsel C, Boddien A, Jackstell R, Jennerjahn R, Dyson PJ, Scopelliti R, Laurenczy G, Beller B. Angew. Chem. Int. Ed. 2010; 49: 9777
    Suche in Google Scholar
  • 24 Jessop PG, Hisao Y, Ikariya T, Noyori R. J. Am. Chem. Soc. 1996; 118: 344
    Suche in Google Scholar
  • 25 Ju P, Chen J, Chen A, Chen L, Yu Y. ACS Sustainable Chem. Eng. 2017; 5: 2516
    Suche in Google Scholar
  • 26 Reddy PG, Kishore Kumar GD, Baskaran S. Tetrahedron Lett. 2000; 41: 9149
    Suche in Google Scholar
  • 27 Katrizky AR, Cahng HX, Yang B. Synthesis 1995; 503
  • 28 Hosseini MS, Sharghi H. J. Org. Chem. 2006; 71: 6652
    Suche in Google Scholar
  • 29 Nasrollahzadeh M, Motahharifar N, Sajjadi M, Aghbolagh AM, Shokouhimehr M, Rajender SV. Green Chem. 2019; 21: 5144
    Suche in Google Scholar
  • 30 Mhoy ED. T, Evans D, Rouden J, Blanchet J. Chem. Eur. J. 2016; 22: 5894
    Suche in Google Scholar
  • 31 Srinivas C, Sajith AM, Yatheesh N, Poornima S, Sandhya NC, Sagar KS, Kumara MN, Rangappa KS, Mantelingu K. J. Org. Chem. 2021; 86: 5530
    Suche in Google Scholar
  • 32 Shamanth S, Chaithra N, Gurukiran M, Mamatha M, Lokanath NK, Rangappa KS, Mantelingu K. Org. Biomol. Chem. 2020; 18: 2678
    Suche in Google Scholar
  • 33 Pandey V, Wang B, Mohan CD, Raquib AR, Rangappa S, Srinivasa V, Fuchs JE, Girish KS, Zhu T, Bender A, Ma L, Yin Z, Rangappa KS, Lobie PE. Proc. Natl. Acad. Sci. U.S.A. 2018; 115: E10505
    Suche in Google Scholar
  • 34 Ramesha AB, Sandhya NC, Pavan KumarC. S, Hiremath M, Mantelingu K, Rangappa KS. New J. Chem. 2016; 40: 7637
    Suche in Google Scholar
  • 35 Suprtha VV, Swarup HA, Vidya G, Vindya KG, Virginie R, Biba C, Franklin J, Sharathkumar SK, Rupa K, Ritu K, Mantelingu K, Ujjayinee R, Gudapureddy R, Depina D, Monica P, Hanumappa A, Subhas SK, Mrinal S, Jean B, Raghavan SC. FEBS J. 2018; 285: 3959
    Suche in Google Scholar
  • 36 Swarup HA, Mantelingu K, Rangappa KS. ChemistrySelect 2018; 3: 703
    Suche in Google Scholar
  • 37 Raghavendra GM, Pavan Kumar CS, Suresha GP, Rangappa KS, Mantelingu K. Chin. Chem. Lett. 2015; 26: 963
    Suche in Google Scholar
  • 38 Swarup HA, Chaithra N, Sandhya NC, Rangappa K, Mantelingu K, Rangappa KS. Synth. Commun. 2019; 49: 2106
    Suche in Google Scholar
  • 39 Srinivas C, Chaithra N, Poornima S, Swarup HA, Sandhya NC, Kumara MN, Mantelingu K. Synth. Commun. 2020; 49: 1486
    Suche in Google Scholar
  • 40 Kumar SV, Yadav SK, Raghava B, Saraiah B, Ila H, Rangappa KS, Hazra A. J. Org. Chem. 2013; 78: 4960
    Suche in Google Scholar
  • 41 Kim SO, Sakchaisri K, Thimmegowda NR, Soung NK, Jang JH, Kim YS, Lee KS, Kwon YT, Asami Y, Erickson RL, Ahn JS, Kim BY. PLOS ONE 2013; 8: 53908
    Suche in Google Scholar
  • 42 Thimmegowda NR, Kavitha CV, Chiruvella KK, Joy O, Rangappa KS, Raghavan SC. Bioorg. Med. Chem. Lett. 2009; 19: 4594
    Suche in Google Scholar
  • 43 Thimmegowda NR, Swamy SN, Kumar CS. A, Kumar YC. S, Chandrappa S, Yip GW, Rangappa KS. Bioorg. Med. Chem. Lett. 2008; 18: 432
    Suche in Google Scholar
  • 44 Chatterjee T, Kumar NT, Das KS. Polyhedron 2017; 127: 68
    Suche in Google Scholar
  • 45 Wu L, Zhong W, Xu B, Wei Z, Liu X. Dalton Trans. 2015; 8013
  • 46 Plater MJ, Barnes P, McDonald LK, Wallace S, Archer N, Gelbrich T, Horton PN, Hursthouse MB. Org. Biomol. Chem. 2009; 7: 1633
    Suche in Google Scholar