Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 19
327
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Simple, Novel Synthesis for 1-Carbamoyl-lH-benzotriazole and Some of Its Analogs

, &
Pages 3354-3365 | Received 24 Feb 2008, Published online: 12 Sep 2008

REFERENCES

  • Bigi , F. ; Maggi , R. ; Sartori , G. Selected syntheses of ureas through phosgene substitutes . Green Chem. 2000 , 2 , 140 – 148 .
  • Katritzky , A. R. ; Kirichenko , N. ; Rogovoy , B. V. Synthesis of mono- and N,N-disubstituted ureas (KF-627HP) . Arkivoc , 2003 , 8 , 8 – 14 .
  • Katritzky , A. R. ; Suzuki , K. ; Wang , Z. Acylbenzotriazoles as advantageous N-, C-, S-, and O-acylating agents . Synlett 2005 , 1656 – 1665 .
  • Katritzky , A. R. ; Lan , X. ; Yang , J. Z. ; Denisko , O. V. Properties and synthetic utility of N-substituted benzotriazoles . Chem. Rev. , 1998 , 98 , 416 .
  • Fieser , L. F. ; Martin , E. L. A comparison of heterocyclic systems with benzene, V: The benzotriazole (azimidobenzene) series . J. Am Chem. Soc. 1935 , 57 , 1835 – 1839 .
  • Jean-Claude , B. J. ; Just , G. Synthesis of bi- and tri-cyclic tetrazepinones . J. Chem. Soc., Perkin Trans. 1991 , 1 , 2525 – 2529 .
  • Vogel , A. I. Textbook of Practical Organic Chemistry, , 4th ed. ; Longman : London , 1978 , p. 734 .
  • Shalaby , M. A. ; Rapoport , H. A general and efficient route to thionoesters via thionoacyl nitrobenzotriazoles . J. Org. Chem. 1999 , 64 , 1065 – 1070 .
  • Katritzky , A. R. ; Witek , R. M. ; Rodriguez-Garcia , V. ; Mohapatra , P. P. ; Rogers , J. W. ; Cusido , J. ; Abdel-Fattah , A. A. A. ; Steel , P. J. Benzotriazole-assisted thioacylation . J. Org.Chem. 2005 , 70 , 7866 – 7881 .
  • Katritzky , A. R. ; Lan , X. ; Yang , J. Z. ; Denisko , O. V. Properties and synthetic utility of N-substituted benzotriazoles . Chem. Rev. 1998 , 98 , 466 – 468 .
  • Katritzky , A. R. ; Yannakopoulou , K. ; Kuzmierkiewicz , W. ; Aurrecoechea , J. M. ; Palenik , G. J. ; Koziol , A. E. ; Szczesniak M. ; Skarjune , R. J. The chemistry of N-substituted benzotriazoles, part 7: The isomeric composition and mechanism of interconversion of some N-(aminomethyl)benzotriazole derivatives . J. Chem. Soc., Perkin Trans. 1 , 1987 , 2673 – 2679 .
  • Gray , A. P. ; Kraus , H. ; Heitmeier , D. E. Pyridylethylation of skatole, benzotriazole and benzimidazole . J. Org.Chem. 1960 , 25 , 1939 – 1943 .
  • Katritzky , A. R. ; Lan , X. ; Yang , J. Z. ; Denisko , O. V. Properties and synthetic utility of N-substituted benzotriazoles . Chem. Rev. 1998 , 98 , 415 .
  • Ogura , H. ; Takayanagi , H. ; Yamazaki , Y. ; Yonezawa , S. ; Takagi , H. ; Kobayashi , S. ; Kamioka , T. ; Kamoshita , K. Studies on heterocyclic compounds, 10: Synthesis of some imidazo [1,2-α]benzimidazoles with potent analgetic activities . J. Med. Chem. 1972 , 15 , 923 – 926 ; they cite North, R. J.; Day, A. R. A study of some 1-alkyl-2,3-dihydroimidazo[1,2-α] benzimidazoles. J. Heterocycl. Chem. 1969, 6, 655–662, as their source for compound 1a in their experimental work. This work contains no mention of the compound. However, the 1H NMR data given here is in very close agreement with the spectrum published in Jean-Claude, B. J.; Just, G. Magn. Reson. Chem. 1992, 30, 572. We found that melting point depends on heating rate. The liquid sample decomposes, solidifies, and remelts at about 310°C (c.f. benzimidazolone).
  • Katritzky , A. R. ; Khashab , N. M. ; Gromova , A. V. Preparations of diversely substituted thiosemicarbazides and N-hydroxythioureas (JC-1696EP). Arkivoc 2006, 3, 226–236.
  • Carbon , J. A. Adjacent nitro and guanidino groups, 11: The base-catalyzed rearrangement of benzotriazine N-oxides to benzotriazoles . J. Org. Chem. 1962 , 27 , 185 – 188 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.