Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Sodium Dodecyl Sulfate‐assisted Synthesis of 1‐(Benzothiazolylamino)methyl‐2‐naphthols in Water

Anil Kumar A B , M. Sudershan Rao A and V. Kameswara Rao A
+ Author Affiliations
- Author Affiliations

A Chemistry Group, Birla Institute of Technology and Science, Pilani 333 031, India.

B Corresponding author. Email: anilkumar@bits‐pilani.ac.in

Australian Journal of Chemistry 63(11) 1538-1540 https://doi.org/10.1071/CH10209
Submitted: 24 May 2010  Accepted: 29 September 2010   Published: 11 November 2010

Abstract

An efficient synthesis of 1‐(benzothiazolylamino)methyl‐2‐naphthols has been developed in water by one‐pot condensation of 2‐naphthol, aldehydes and 2‐aminobenzothiazole catalyzed by sodium dodecyl sulfate. Advantages of the methodology include a very short reaction time, excellent yields and catalytic use of the sodium dodecyl sulfate.


References

[1]  (a) R. W. Van De Water, T. R. R. Pettus, Tetrahedron 2002, 58, 5367.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XkvVegtbg%3D&md5=02c9897808fdccbb5567ca5e68060afeCAS | 19079773PubMed |
      (b) Y. Chiang, A. J. Kresge, Y. Zhu, Pure Appl. Chem. 2000, 72, 2299.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  S. H. Mashraqui, M. B. Patil, H. D. Mistry, S. Ghadigaonkar, A. Meetsmay, Chem. Lett. 2004, 33, 1058.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmvVKls78%3D&md5=ece5e0dfab211daa6a7ea06e0bb7896bCAS |

[3]  M. J. Adler, S. W. Baldwin, Tetrahedron Lett. 2009, 50, 5075.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXoslCqu70%3D&md5=ab4ca6a1c33af2c239f1204e5ce33380CAS |

[4]  J. S. Yadav, B. V. Subba Reddy, K. Sadashiv, B. Padmavani, Adv. Synth. Catal. 2004, 346, 607.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXlt1Ojsbc%3D&md5=61abb454a1f4222725ee731d443d8ef8CAS |

[5]  H. Sugimoto, S. Nakamura, T. Ohwada, Adv. Synth. Catal. 2007, 349, 669.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXktVWjurk%3D&md5=d45b0709fb2c7f7579a754c2e0676a7fCAS |

[6]  (a) L. Diao, C. Yang, P. Wan, J. Am. Chem. Soc. 1995, 117, 5369.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlsFert7k%3D&md5=1cc6c072b3cd1dde784e7a4ef4064806CAS |
      (b) P. Wan, B. Barker, L. Diao, M. Fischer, Y. Shi, Can. J. Chem. 1996, 74, 465.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  A. F. Barrero, J. F. Quılez del Moral, M. M. Herrador, P. Arteaga, M. Cortes, J. Benites, A. Rosellon, Tetrahedron 2006, 62, 6012.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XkvFykur4%3D&md5=876a32b68868557ec0403c5c3f8da52cCAS |

[8]  R. Rodriguez, R. M. Adlington, J. E. Moses, A. Cowley, J. E. Baldwin, Org. Lett. 2004, 6, 3617.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmvFCgs70%3D&md5=af208c480992a3fc33c9c42fa5d55655CAS | 15387562PubMed |

[9]  (a) Y.‐L. Mao, Y. Boekelheide, Proc. Natl. Acad. Sci. USA 1980, 77, 1732.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXls1Ogs7c%3D&md5=9343b32179ec02b7ec08a44944f8ff45CAS |
      (b) T. Inoue, S. Inoue, K. Sato, Bull. Chem. Soc. Jpn. 1990, 63, 1062.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  A. E. Mattson, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 4508.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjt1ymtr4%3D&md5=add339a4d197018b1e5c8e285f0db932CAS | 17378561PubMed |

[11]  S. J. Gharpure, A. M. Sathiyanarayanan, P. Jonnalagadda, Tetrahedron Lett. 2008, 49, 2974.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXktlyqsb4%3D&md5=dd5f615066a5d9320299dc2c1b3f8f33CAS |

[12]  (a) C.‐J. Li, L. Chen, Chem. Soc. Rev. 2006, 35, 68.
         | Crossref | GoogleScholarGoogle Scholar | 16365643PubMed |
      (b) U. M. Lindström, Chem. Rev. 2002, 102, 2751.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. C. Hailes, Org. Process Res. Dev. 2007, 11, 114.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) M. Fousteris, C. Chevrin, J. Le Bras, J. Muzart, Green Chem. 2006, 8, 522.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xltlars7c%3D&md5=ff1b27e376070fc50d0f26cf017fbe0fCAS |
      (b) G. L. Khatik, R. Kumar, A. K. Chakraborti, Org. Lett. 2006, 8, 2433.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Ghosh, R. Deya, K. Chattopadhyaya, B. C. Ranu, Tetrahedron Lett. 2009, 50, 4892.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  S. M. Reed, J. E. Hutchison, J. Chem. Educ. 2000, 77, 1627.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXot1Orsr0%3D&md5=0d6cedde4cb3a843d807f8ce49a5562dCAS |

[15]  (a) A. K. Chakraborti, S. Rudrawar, K. B. Jadhav, G. Kaur, S. V. Chankeshwara, Green Chem. 2007, 9, 1335.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlemu7fK&md5=c38c8e86da8d22b7bc59c2bdaa9971ccCAS |
      (b) P. A. Grieco, E. B. Brandes, S. McCann, J. D. Clark, J. Org. Chem. 1989, 54, 5849.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  (a) Y. Mori, K. Kakumoto, K. Manabe, S. Kobayashi, Tetrahedron Lett. 2000, 41, 3107.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjt1Citbw%3D&md5=186e149d2ba2f0cd6fe78ad4b89c9775CAS |
      (b) K. Manabe, S. Kobaashi, Tetrahedron Lett. 1999, 40, 3773.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  (a) S. D. Srivastava, J. P. Sen, Indian J. Chem. 2008, 47B, 1583.
         | 1:CAS:528:DC%2BD1MXhvVyhsg%3D%3D&md5=1180835edcd1fedd3023120db4b06353CAS |
      (b) Z.‐G. Le, J.‐P. Xu, H.‐Y. Rao, M. Ying, J. Heterocycl. Chem. 2006, 43, 1123.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  (a) A. Shaabani, A. Rahmati, E. Farhangi, Tetrahedron Lett. 2007, 48, 7291.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVGju7vO&md5=8eecf859f6bdf21ca6eb028216f6a7f1CAS |
         (b) (b) A. Ohanian, S. Javanshir, M. M. Heravi, F. F. Bamoharram, 13th International Electronic Conference on Synthetic Organic Chemistry (ECSOC‐13) 2009.

[19]  (a) A. Kumar, M. S. Rao, I. Ahmad, B. Khungar, Aust. J. Chem. 2009, 62, 322.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXltVyqu7w%3D&md5=a6d2a1976ab77624e0980114c3c0d960CAS |
      (b) A. Kumar, I. Ahmad, M. S. Rao, G. Patel, D. Kumar, Indian J. Chem. 2009, 48B, 611.
      (c) A. Kumar, I. Ahmad, M. S. Rao, Can. J. Chem. 2008, 86, 899.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  A. Kumar, M. K. Gupta, M. Kumar, Tetrahedron Lett. 2010, 51, 1582.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhvF2qt7g%3D&md5=2600af48e6a3285a2a81ae68e8e35e7dCAS |