Processing, Please wait...

  • Home
  • About Us
  • Search:
  • Advanced Search

Growing Science » Current Chemistry Letters » Synthesis of fused heterocycles from 2-aryl-5-(chlorosulfonyl)-1,3-oxazole-4-carboxylates and α-aminoazoles involving the Smiles rearrangement

Journals

  • IJIEC (747)
  • MSL (2643)
  • DSL (668)
  • CCL (508)
  • USCM (1092)
  • ESM (413)
  • AC (562)
  • JPM (271)
  • IJDS (912)
  • JFS (91)
  • HE (32)
  • SCI (26)

CCL Volumes

    • Volume 1 (23)
      • Issue 1 (7)
      • Issue 2 (5)
      • Issue 3 (6)
      • Issue 4 (5)
    • Volume 2 (26)
      • Issue 1 (7)
      • Issue 2 (6)
      • Issue 3 (6)
      • Issue 4 (7)
    • Volume 3 (30)
      • Issue 1 (7)
      • Issue 2 (10)
      • Issue 3 (8)
      • Issue 4 (5)
    • Volume 4 (21)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (6)
      • Issue 4 (5)
    • Volume 5 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 6 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 7 (15)
      • Issue 1 (4)
      • Issue 2 (4)
      • Issue 3 (4)
      • Issue 4 (3)
    • Volume 8 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 9 (20)
      • Issue 1 (5)
      • Issue 2 (5)
      • Issue 3 (5)
      • Issue 4 (5)
    • Volume 10 (43)
      • Issue 1 (5)
      • Issue 2 (7)
      • Issue 3 (17)
      • Issue 4 (14)
    • Volume 11 (43)
      • Issue 1 (14)
      • Issue 2 (11)
      • Issue 3 (10)
      • Issue 4 (8)
    • Volume 12 (78)
      • Issue 1 (21)
      • Issue 2 (22)
      • Issue 3 (20)
      • Issue 4 (15)
    • Volume 13 (68)
      • Issue 1 (23)
      • Issue 2 (17)
      • Issue 3 (16)
      • Issue 4 (12)
    • Volume 14 (68)
      • Issue 1 (20)
      • Issue 2 (13)
      • Issue 3 (22)
      • Issue 4 (13)
    • Volume 15 (13)
      • Issue 1 (13)

Keywords

Supply chain management(166)
Jordan(161)
Vietnam(149)
Customer satisfaction(120)
Performance(113)
Supply chain(110)
Service quality(98)
Competitive advantage(95)
Tehran Stock Exchange(94)
SMEs(87)
optimization(86)
Financial performance(83)
Trust(83)
TOPSIS(83)
Sustainability(81)
Job satisfaction(80)
Factor analysis(78)
Social media(78)
Knowledge Management(77)
Artificial intelligence(77)


» Show all keywords

Authors

Naser Azad(82)
Mohammad Reza Iravani(64)
Zeplin Jiwa Husada Tarigan(63)
Endri Endri(45)
Muhammad Alshurideh(42)
Hotlan Siagian(39)
Jumadil Saputra(36)
Dmaithan Almajali(36)
Muhammad Turki Alshurideh(35)
Barween Al Kurdi(32)
Ahmad Makui(32)
Basrowi Basrowi(31)
Hassan Ghodrati(31)
Mohammad Khodaei Valahzaghard(30)
Sautma Ronni Basana(29)
Shankar Chakraborty(29)
Ni Nyoman Kerti Yasa(29)
Sulieman Ibraheem Shelash Al-Hawary(28)
Prasadja Ricardianto(28)
Haitham M. Alzoubi(27)


» Show all authors

Countries

Iran(2183)
Indonesia(1290)
India(787)
Jordan(786)
Vietnam(504)
Saudi Arabia(453)
Malaysia(441)
United Arab Emirates(220)
China(206)
Thailand(153)
United States(111)
Turkey(106)
Ukraine(104)
Egypt(98)
Canada(92)
Peru(88)
Pakistan(85)
United Kingdom(80)
Morocco(79)
Nigeria(78)


» Show all countries

Current Chemistry Letters

ISSN 1927-730x (Online) - ISSN 1927-7296 (Print)
Quarterly Publication
Volume 7 Issue 4 pp. 101-110 , 2018

Synthesis of fused heterocycles from 2-aryl-5-(chlorosulfonyl)-1,3-oxazole-4-carboxylates and α-aminoazoles involving the Smiles rearrangement Pages 101-110 Right click to download the paper Download PDF

Authors: Maryna Kachaeva, Stepan Pilyo, Sergiy Popilnichenko, Andrii Kornienko, Eduard Rusanov, Volodymyr Prokopenko, Vladimir Zyabrev, Volodymyr S. Brovarets

DOI: 10.5267/j.ccl.2018.9.001

Keywords: 1, 3-Oxazole-5-sulfonyl chloride, Aminoazole, Smiles rearrangement, [1, 3]Oxazolo[5, 4-d]pyrimidine

Abstract: Reaction of methyl 2-aryl-5-(chlorosulfonyl)-1,3-oxazole-4-carboxylates with 1H-pyrazol-5-amines and 1H-1,2,4-triazol-5-amines proceeds with the participation of endocyclic aminoazole nitrogen atoms to yield products containing a primary amino group. Being treated by sodium hydride these products undergo a further transformation into the tricyclic compounds. It has been shown that the cyclocondensation pathway includes the Smiles rearrangement with extrusion of SO2 followed by the elimination of MeOH. This reaction sequence is a convenient approach to the synthesis of new annulated [1,3]oxazolo[5,4-d]pyrimidine derivatives.

How to cite this paper
Kachaeva, M., Pilyo, S., Popilnichenko, S., Kornienko, A., Rusanov, E., Prokopenko, V., Zyabrev, V & Brovarets, V. (2018). Synthesis of fused heterocycles from 2-aryl-5-(chlorosulfonyl)-1,3-oxazole-4-carboxylates and α-aminoazoles involving the Smiles rearrangement.Current Chemistry Letters, 7(4), 101-110.

Refrences
1. Palmer D. C., and Venkatraman S. (2003) Synthesis and reactions of oxazoles, in: Palmer D. C. (Ed) Oxazoles: Synthesis, Reactions, and Spectroscopy. Part A. Wiley, 127.
2. Barbey S., Goossens L., Taverne T., Cornet J., Choesmel V., Rouaud C., Gimeno G., Yannic-Arnoult S., Michaux C., Charlier C., Houssin R., and Henichart J.-P. (2002) Synthesis and activity of a new methoxytetrahydropyran derivative as dual cyclooxygenase-2/5-lipoxygenase inhibitor. Bioorg. Med. Chem. Lett., 12 (5) 779–782.
3. Kachaeva M. V., Pilyo S. G., Kornienko A. M., Prokopenko V. M., Zhirnov V. V., Prichard M. N., Keith K. A., Yang G., Wang H.-K., Banerjee N. S., Chow L. T., Broker T. R., and Brovarets V. S. (2017) In vitro activity of novel 1,3-oxazole derivatives against human papillomavirus. Ibnosina J. Med. Biomed. Sci., 9 (4) 111–118.
4. Kornienko A. N., Pil'o S. G., Prokopenko V. M., and Brovarets V. S. (2014) Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines Rus. J. Gen. Chem., 84 (8) 1555–1560.
5. Pozharskii A. F., Soldatenkov A. T., and Katritzky A. R. (2011) Heterocycles in Life and Society, 2th Ed, Wiley, 144–146.
6. Kornienko A. N., Pil’o S. G., Kozachenko A. P., Prokopenko V. M., Rusanov E. B., and Brovarets V. S. (2014) Reaction of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides with 5-amino-1H-pyrazoles and 5-amino-1H-1,2,4-triazole. Chem. Het. Comp., 50 (1) 76–86.
7. Ege G., and Franz H. (1984) Aminopyrazoles. V [1]. Structure assignment of lH-pyrazol-3- and 5 amines by means of the 1H NMR δ(4-H)-values of their exo-N-toluenesulfonyl derivatives. J. Heterocyclic Chem., 21 (3) 689–695.
8. Backer H. J., and De Jonge J. (1943) Dérivés de la sulfanilamide renfermant l'anneau 1,2,4‐triazol. Recl. Trav. Chim. Pays-Bas., 62 (3) 158–162.
9. Plesniak K., Zarecki A., and Wicha J. (2007) The smiles rearrangement and the Julia-Kocienski olefination reaction. Top. Curr. Chem., 275 (46) 163–250.
10. Plescia S., Agozzino P, and Fabra I. (1977) A facile synthesis of some pyrazolo[1,5-b]-1,2,4-benzothiadiazepin-5(4H)ones-10,10-dioxides. A new ring system. J. Heterocyclic Chem., 14 (8) 1431–1432.
11. Sheldrick G. (2008) A short history of SHELX. Acta Cryst., Sect. A., 64 (Pt 1) 112–122.
  • 17
  • 1
  • 2
  • 3
  • 4
  • 5

Journal: Current Chemistry Letters | Year: 2018 | Volume: 7 | Issue: 4 | Views: 1894 | Reviews: 0

Related Articles:
  • Regioselective synthesis of bicyclic 1,3,5-triazepine system starting from ...
  • A facile and efficient protocol for the synthesis of 2-amino-3-cyano-4H-pyr ...
  • Single crystal X-ray structure of 3-amino-5-(4-chlorophenyl)pyridazine-4-ca ...
  • Vilsmeier-Haack reagent: A facile synthesis of 2-(4-chloro-3,3-dimethyl-7-p ...
  • The synthesis of 2-arylquinoxaline derivatives

Add Reviews

Name:*
E-Mail:
Review:
Bold Italic Underline Strike | Align left Center Align right | Insert smilies Insert link URLInsert protected URL Select color | Add Hidden Text Insert Quote Convert selected text from selection to Cyrillic (Russian) alphabet Insert spoiler
winkwinkedsmileam
belayfeelfellowlaughing
lollovenorecourse
requestsadtonguewassat
cryingwhatbullyangry
Security Code: *
Include security image CAPCHA.
Refresh Code

® 2010-2026 GrowingScience.Com