본문 바로가기
KERD
논문KCI 등재

Oxidative Cyclisation Based One-Pot Synthesis of 3-Substituted[1,2,4]triazolo[4,3-b]pyridazines Using Me4NBr/Oxone

Jayaraman Sembian Ruso|Rajendran Senthil Kumaran|Rajendiran Nagappan
대한화학회|2013.10|대한화학회지 (Journal of the Korean Chemical Society)|제57권 제5호|pp. 606-611|DOI http://dx.doi.org/10.5012/jkcs.2013.57.5.606

2

조회

0

다운로드

1

인용

0

참고문헌

키워드

124-TriazolopyridazineTetramethylammonium bromideOxoneAromatic aldehyde
주제분류화학

초록

A facile one-pot syhthesis of 3-substituted triazolopyridazine and thieno-triazolopyridazine derivatives is described. This protocol involves the preparation of heteroaryl hydrazone from the aldehyde and pyridazinohydrazine derivative followed by subjecting the intermediate directly to oxidative cyclization to assemble the desired 1,2,4-triazloe moiety by employing the mixture of Me4NBr and oxone. This condition is efficient and is able to tolerate wide range of functional groups.

Abstract

A facile one-pot syhthesis of 3-substituted triazolopyridazine and thieno-triazolopyridazine derivatives is described. This protocol involves the preparation of heteroaryl hydrazone from the aldehyde and pyridazinohydrazine derivative followed by subjecting the intermediate directly to oxidative cyclization to assemble the desired 1,2,4-triazloe moiety by employing the mixture of Me4NBr and oxone. This condition is efficient and is able to tolerate wide range of functional groups.

참고문헌 (49)

  1. Ulusoy, N., , II Farmaco, 56, pp.947~952 (2001)
  2. Papakostantinou, S., , II Farmaco, 57, pp.973~977 (2002)
  3. Kucukguzel, I. I., , Bioorg. Med. Chem. Lett, 11, pp.1703~1707 (2001)
  4. Patel, N. B., , Eur. J. Med. Chem, 45, pp.4293~4299 (2010)
  5. Shiradkar, M., , Eur. J. Med. Chem, 42, pp.807~816 (2007)
  6. Parmar, S. S., , J. Med. Chem, 15, pp.999~1000 (1972)
  7. Wang, L. C., , Molecules, 11, pp.169~176 (2006)
  8. Zitouni, G. T., , Arch. Pharm. Chem. Life. Sci, 11, pp.586~590 (2007)
  9. Sarva, M. C., , Cheminform, 33, pp.2002~2004 (2010)
  10. Holla, B. S., , Eur. J. Med. Chem, 38, pp.759~767 (2003)
  11. Parmar, S. S., , J. Pharm. Sci, 66, pp.971~975 (1977)
  12. Shimizu, S., , Org. Process Res. Dev, 11, pp.1055~1058 (2007)
  13. Marino, J. P. Jr., , J. Med. Chem, 50, pp.3777~3785 (2007)
  14. Bower, J. D., , J. Chem. Soc, pp.727~732 (1957)
  15. Gibson, M. S., , Tetrahedron, 19, pp.1587~1589 (1963)
  16. Pollak, A., , Tetrahedron, 22, pp.2073~2079 (1966)
  17. El-Gazzar, A. B., , Molecules, 5, pp.835~850 (2000)
  18. Abdel-Fattah, B., , J. Chin. Chem. Soc, 53, pp.403~412 (2006)
  19. Shawali, A. S., , Tetrahedron, 64, pp.10339~10558 (2008)
  20. Shawali, A. S., , Heterocycles, 75, pp.1479~1488 (2008)
  21. Shawali, A. S., , Tetrahedron, 58, pp.8559~8564 (2002)
  22. pyrimidine Derivatives by Oxidative Cyclization Using Alumina-supported Calcium Hypochlorite, "Bulletin of the Korean Chemical Society", 2010, 2242~2246, pp.대한화학회
  23. Mogilaiah, K., , Indian J. Chem, 50, pp.1187~1191 (2011)
  24. Thiel, O. R., , Angew. Chem. Int. Ed, 49, pp.8395~8398 (2010)
  25. Staben, S., , Angew. Chem. Int. Ed, 49, pp.325~328 (2010)
  26. Unqureanu, M., , Ann. Pharm. Fr, 55, pp.69~72 (1997)
  27. Galtie, C., , Antivir. Chem. & Chemother, 14, pp.177~182 (2003)
  28. Islam, M., , Acta Pol Pharm, 65, pp.441~447 (2008)
  29. Yassin, F. A., , Chem. Heterocycl. Comp, 45, pp.997~1003 (2009)
  30. Zhou, J., , Phosphorus. Sulfur. Silicon Relat. Elem, 186, pp.81~87 (2010)
  31. Bloomer, L.C., , Cancer Res, 42, pp.100~106 (1982)
  32. Katz, D. J., , J. Med. Chem, 25, pp.813~821 (1982)
  33. Corina, M., , J. Org. Chem, 56, pp.5466~5468 (1991)
  34. Abubshait, S. A., , Molecules, 12, pp.25~42 (2007)
  35. Yokoyama, M., , Chem Lett, 517, pp.265~268 (1994)
  36. Mantu, D., , Eur. J. Med. Chem, 45, pp.5164~5168 (2010)
  37. Malinka, W., , II Farmaco, 59, pp.457~462 (2004)
  38. Albright, J. D., , J. Med. Chem, 24, pp.592~600 (1981)
  39. Biagi, G., , II Farmaco, 51, pp.601~608 (1996)
  40. Atack, J. R., , J. Pharmacol Exp Ther, 332, pp.17~25 (2010)
  41. Licata, S. C., , Neuropharmacology, 58, pp.357~364 (2010)
  42. El-Dean, A. M. K., , Cheminform, 35, pp.321~344 (2004)
  43. Singh, A. K., , Indian J. Pharm. Sci, 67, pp.210~215 (2005)
  44. Pieretti, S., , Life Sci, 79, pp.791~800 (2006)
  45. Zaher, A. F. A., , Bull. Fac. Pharm. Cairo. Univ, 47, pp.69~75 (2009)
  46. Street, L., , J. Med. Chem, 47, pp.3642~3657 (2004)
  47. Shamroukh, A. H., , Arch. Pharm, 341, pp.223~230 (2008)
  48. Albrecht, B. K., , J. Med. Chem, 51, pp.2879~2882 (2008)
  49. thiophene-2-carboxylic acid in four steps,

관련 논문AI추천

Antimicrobial Activities of Novel 3-Substituted [1,2,4] Triazolo[4,3-b]pyridazines DerivativesChowdappa Srinivas, Jayaraman Sembian Ruso, Konappa Narasimha murthy, Krishnamurthy Soumya, Nagappan Rajendiran대한화학회 · 대한화학회지2014 · 제58권 제4호An Expeditious Room Temperature Stirring Method for the Synthesis of Isoxazolo[5,4-b]quinolinesBapurao B. Shingate, Kirti S. Niralwad, Murlidhar S. Shingare대한화학회 · 대한화학회지2011 · 제55권 제5호Synthesis of New Pyrazolo[5,1-c]triazine, Triazolo[5,1-c]triazine, Triazino[4,3-b]indazole and Benzimidazo[2,1-c]triazine Derivatives Incorporating Chromen-2-one MoietyMohamed A. Khalil, Mohamed A. Raslan, Samia M. Sayed대한화학회 · 대한화학회지2013 · 제57권 제5호Synthesis and Characterization of 1-Benzofuran-2-yl thiadiazoles, Triazoles and Oxadiazoles by Conventional and Non-conventional MethodsAnanta D. Shinde, Bapurao B. Shingate, Bhima Y. Kale, Murlidhar S. Shingare대한화학회 · 대한화학회지2010 · 제54권 제5호Facile Synthesis of 2-Phenylthieno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidine Derivatives as a New Ring System송양헌대한화학회 · 대한화학회지2010 · 제54권 제6호New Synthesis of Perhydrotriazolotriazoles Catalyzed by TiCl₄ under Ambient ConditionsJ. Safari, M. Ghotbinejad, S. Gandomi-Ravandi대한화학회 · 대한화학회지2012 · 제56권 제1호

이 간행물의 다른 논문 (14건)

Borate 완충용액에서 니켈 회전원판전극의 부식과 부동화김연규pp. 533-539분자의 논랜덤 분포가 기체의 상태방정식에 미치는 영향정해영pp. 540-5462 단계 양극 산화를 이용한 ZrO2 나노 다공성 산화막의 제조와 특성에 관한 연구강위경, 최세경, 신익수, 서의영pp. 547-553계산화학적 방법을 통한 β-D-glucopyranose 구조 연구이상민, 김진아, 안익성, 민병진, 양지현pp. 554-559Synthesis, Characterization and Spectrophotometric Studies of Seven Novel Antibacterial Hydrophilic Iron(II) Schiff Base Amino Acid ComplexesAli M. Shaker, Lobna A. E. Nassr, Mohamed S. S. Adam, Ibrahim M. A. Mohamedpp. 560-567
원문 보기