Zinc-Mediated Facile and Efficient Chemoselective S-Alkylation of 5-Aryl-1,3,4-oxadiazole-2-thiols in the Absence of Base

REFERENCES

• (a) Tully , W. R. ; Cardner , C. R. ; Gillespie , R. J. ; Westwood , R. 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors . J. Med. Chem. 1991 , 34 ( 7 ), 2060 – 2067 ; (b) Chen , C. Y. ; Senanayake , C. H. ; Bill , J. C. H. ; Larsen , R. D. ; Verhoeven , T. R. ; Reider , P. J. Improved Fischer indole reaction for the preparation of N,N-dimethyltryptamines: Synthesis of L-695,894, a potent 5-HT1D receptor agonist . J. Org. Chem. 1994 , 59 ( 13 ), 3738 – 3741 ; (c) Dogan , H. N. ; Duran , A. ; Rollas , S. ; Sener , G. ; Uysal , M. K. ; Gulen , D. Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities . Bioorg. Med. Chem. 2002 , 10 , 2893 – 2898 .
   PubMed Web of Science ®Google Scholar
• (a) Shi , W. ; Qian , X. ; Zhang , R. ; Song , G. Synthesis and quantitative structure–activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles . J. Agric. Food Chem. 2001 , 49 ( 1 ), 124 – 130 ; (b) Chen , H. ; Li , Z. ; Han , Y. Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (thiadiazoles) . J. Agric. Food Chem. 2000 , 48 ( 11 ), 5312 – 5315 .
   PubMed Web of Science ®Google Scholar
• (a) Meng , H. ; Hung , W. Novel photoluminescent polymers containing oligothiophene and m-phenylene-1,3,4-oxadiazole moieties: Synthesis and spectroscopic and electrochemical studies . J. Org. Chem. 2000 , 65 ( 13 ), 3894 – 3901 ; (b) Bottino , F. A. ; Pasquale , G. D. ; Iannelli , P. Synthesis, characterization, and study of the thermal properties of new poly(arylene ether 1,3,4-oxadiazole)s . Macromolecules 2001 , 34 ( 1 ), 33 – 37 ; (c) Chen , Z.-K. ; Meng , H. ; Lai , Y.-H. ; Huag , W. Photoluminescent poly(p-phenylenevinylene)s with an aromatic oxadiazole moiety as the side chain: Synthesis, electrochemistry, and spectroscopy study . Macromolecules 1999 , 32 ( 13 ), 4351 – 4358 .
   PubMed Web of Science ®Google Scholar
• (a) Perez , M. A. ; Bermejo , J. M. Synthesis of multidentate 1,3,4-oxadiazole-, imine-, and phenol-containing macrocycles . J. Org. Chem. 1993 , 58 ( 9 ), 2628 – 2630 ; (b) Lee , D. W. ; Kwon , K.-Y. ; Jin , J. I. ; Park , Y. ; Kim , Y.-R. ; Hwang , I.-W. Luminescence properties of structurally modified PPVs: PPV derivatives bearing 2-(4-tert-butylphenyl)-5-phenyl-1,3,4-oxadiazole pendants . Chem. Mater. 2001 , 13 ( 2 ), 565 – 574 .
   Web of Science ®Google Scholar
• Ogata , M. ; Atobe , H. ; Kushida , H. ; Yamamoto , K. In vitro sensitivity of mycoplasmas isolated from various animals and sewage to antibiotics and nitrofurans . J. Antibiot. 1971 , 24 ( 7 ), 443 – 451 .
   PubMedGoogle Scholar
• Mullican , M. D. ; Wilson , M. W. ; Conner , D. T. ; Kostlan , C. R. ; Schrier , D. J. ; Dyer , R. D. Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles as orally active, nonulcerogenic anti-inflammatory agents . J. Med. Chem. 1993 , 36 ( 8 ), 1090 – 1099 .
   PubMed Web of Science ®Google Scholar
• Boschelli , D. H. ; Connor , D. T. ; Bornemeier , D. A. ; Dyer , R. D. ; Kennedy , J. A. ; Kuipers , P. J. ; Okonkwo , G. C. ; Schrier , D. J. ; Wright , C. D. 1,3,4-Oxadiazole, 1,3,4-thiadiazole, and 1,2,4-triazole analogs of the fenamates: In vitro inhibition of cyclooxygenase and 5-lipoxygenase activities . J. Med. Chem. 1993 , 36 ( 13 ), 1802 – 1810 .
   PubMed Web of Science ®Google Scholar
• Raman , K. ; Singh , K. H. ; Salzman , S. K. ; Parmar , S. S. Substituted thiosemicarbazides and corresponding cyclized 1,3,4-oxadiazoles and their anti-inflammatory activity. J. Pharm. Sci. 1993, 82(2), 167–169.
   PubMed Web of Science ®Google Scholar
• Husain , M. I. ; Kumar , A. ; Srivastava , R. C. Synthesis of N-(2-naphthyloxy acetyl)thiosemicarbazides and 2-arylamino-5-(2-naphthyloxymethyl)-1,3,4-thiodiazoles/oxadiazoles as oral hypoglycemic agents . Current Sci. 1986 , 55 ( 14 ), 644 – 646 .
   Web of Science ®Google Scholar
• Giri , S. ; Singh , H. ; Yadav , L. D. S. Studies in oxadiazoles synthesis of some 2-mercapto-1,3,4-oxadiazoles and related compounds as potential fungicides . Agr. Biol. Chem. 1976 , 40 ( 1 ), 17 – 21 .
   Web of Science ®Google Scholar
• Adhikari , V. A. ; Badiger , V. V. Synthesis and biological activities of isoxazolo [5,4-d] pyrimidinyl-oxymethyl-thiadiazoles, -oxadiazoles, and -triazoles . Indian J. Chem. 1988 , 27B , 542 – 547 .
   Google Scholar
• Sahin , G. ; Palaska , E. ; Kelicen , P. ; Demirdamar , R. ; Altinok , G. Synthesis of some new 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, and 1,2,4-triazole-3-thiones and their anti-inflammatory activities . Arzneim.-Forsch./Drug Res. 2001 , 51 ( 1 ), 478 – 484 .
   PubMedGoogle Scholar
• Chin Tan , T. M. ; Chen , Y. ; Kong , K. H. ; Bai , J. ; Li , Y. ; Lim , S. G. ; Hong Ang , T. ; Lam , Y. Synthesis and the biological evaluation of 2-benzenesulfonylalkyl-5-substituted-sulfanyl-[1,3,4]-oxadiazoles as potential anti-hepatitis B virus agents . Antiviral Res. 2006 , 71 ( 1 ), 7 – 14 .
   PubMed Web of Science ®Google Scholar
• Facor , D. A. ; Johnson , D. S. ; Powers , J. J. ; Li , T. ; Madabattula , R. Synthesis of chromanyl and dihydrobenzofuranyl piperazines . Tetrahedron Lett. 2007 , 48 ( 17 ), 3039 – 3041 .
   Web of Science ®Google Scholar
• (a) Vacca , J. P. ; Dorsey , B. D. ; Schleif , W. A. ; Levine , R. B. ; McDaniel , S. L. ; Darke , P. L. ; Zugay , J. ; Quintero , J. C. ; Blahy , O. M. ; Sardana , B. B. ; Schlabach , A. J. ; Graham , P. I. ; Condra , J. H. ; Gotlib , L. ; Holloway , M. K. ; Lin , J. ; Chen , I. W. ; Vastag , K. ; Ostovic , D. ; Anderson , P. S. ; Emini , E. A. ; Huff , J. R. L-735,524: An orally bioavailable human immunodeficiency virus type 1 protease inhibitor . Proc. Natl. Acad. Sci. USA 1994 , 91 , 4096 – 4100 ; (b) Vacca , J. P. ; Dorsey , B. D. ; Schleif , W. A. ; Levine , R. B. ; McDaniel , S. L. ; Darke , P. L. ; Zugay , J. ; Quintero , J. C. ; Blahy , O. M. ; Sardana , B. B. ; Schlabach , A. J. ; Graham , P. I. ; Condra , J. H. ; Gotlib , L. ; Holloway , M. K. ; Lin , J. ; Chen , I. W. ; Vastag , K. ; Ostovic , D. ; Anderson , P. S. ; Emini , E. A. ; Huff , J. R. L-735,524: The design of a potent and orally bioavailable HIV protease inhibitor . J. Med. Chem. 1994 , 37 ( 21 ), 3443 – 3451 ; (c) Askin , D. ; Eng , K. K. ; Rossen , K. ; Purick , R. M. ; Wells , K. M. ; Volante , R. P. ; Reider , P. J. Highly diastereoselective reaction of a chiral, nonracemic amide enolate with (S)-glycidyl tosylate: Synthesis of the orally active HIV-l protease inhibitor L-735,524 . Tetrahedron Lett. 1994 , 35 ( 5 ), 673 – 676 ; (d) Rossen , K. ; Weissman , S. A. ; Sagar , J. ; Reamer , R. A. ; Askin , D. A. ; Volante , R. P. ; Reider , P. J. Asymmetric hydrogenation of tetrahydropyrazines: Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir . Tetrahedron Lett. 1995 , 36 ( 36 ), 6419 – 6422 .
   PubMedGoogle Scholar
• Cliffe , I. A. ; Fletcher , A. Advances in 5-HT1A antagonist research . Drugs Future 1993 , 18 ( 7 ), 631 – 642 .
   Google Scholar
• Siracusa , M. A. ; Salerno , L. ; Modica , M. N. ; Pittal , V. ; Romeo , G. ; Amato , M. E. ; Nowack , M. ; Bojarski , A. J. ; Mereghetti , I. ; Cagnotto , A. ; Mennini , T. Synthesis of new arylpiperazinylalkylthiobenzimidazole, benzothiazole, or benzoxazole derivatives as potent and selective 5-HT1A serotonin receptor ligands . J. Med. Chem. 2008 , 51 ( 15 ), 4529 – 4538 .
   PubMed Web of Science ®Google Scholar
• Afshin , Z. ; Mehrdad , F. ; Bijan , S. ; Avideh , A. ; Hamid , R. K. ; Vahideh , Z. ; Sayyed , A. T. ; Abbas , S. Design and synthesis of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4-oxadiazoles as benzodiazepine receptor agonists . Bioorg. Med. Chem. Lett. 2005 , 15 ( 12 ), 3126 – 3129 .
   PubMed Web of Science ®Google Scholar
• El-Emam , A. A. ; Al-Deeb , O. A. ; Al-Omar , M. ; Lehmann , J. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg. Med. Chem. 2004, 12(19), 5107–5113.
   PubMed Web of Science ®Google Scholar
• Milda , M. B. ; Virginija , J. ; Giedrute , M. ; Emilija , U. ; Romualdas , S. ; Povilas , V. Synthesis and anti-inflammatory activity of derivatives of 5-[(2-disubstituted amino-6-methyl-pyrimidin-4-yl)-sulfanyl methyl]-3H-1,3,4-oxadiazole-2-thiones . Farmaco 2004 , 59 , 767 – 774 .
   Google Scholar
• Li , Y. ; Liu , J. ; Zhang , H. ; Yang , X. ; Liu , Z. Stereoselective synthesis and fungicidal activities of (E)-a-(methoxyimino)-benzeneacetate derivatives containing 1,3,4-oxadiazole ring . Bioorg. Med. Chem. Lett. 2006 , 16 ( 8 ), 2278 – 2282 .
   PubMed Web of Science ®Google Scholar
• Farghaly , A. R. ; El-Kashef , H. Synthesis of some new azoles with antiviral potential . Arkivoc 2006 , 11 , 76 – 90 .
   Google Scholar
• (a) Arora , R. ; Paul , S. ; Gupta , R. A mild and efficient procedure for the conversion of aromatic carboxylic esters to secondary amides . Can. J. Chem. 2005 , 83 ( 8 ), 1137 – 1140 ; (b) Bandgar , B. P. ; Pandit , S. S. ; Nagargoje , S. P. Zinc-mediated simple and practical synthesis of sulfides . Sulfur Lett. 2002 , 25 ( 6 ), 247 – 249 .
   Web of Science ®Google Scholar
• (a) Murty , M. S. R. ; Rami Reddy , N. ; Yadav , J. S. Zinc-mediated novel and efficient method for N-sulfonylation of amines in the absence of base . J. Sulfur Chem. 2006 , 27 ( 6 ), 589 – 593 ; (b) Murty , M. S. R. ; Jyothirmai , B. ; Radha Krishna , P. ; Yadav , J. S. Zinc-mediated alkylation of cyclic secondary amines . Synth. Commun. 2003 , 33 ( 14 ), 2483 – 2486 .
   Google Scholar
• Sarva , M. C. ; Romeo , G. ; Guerrera , F. ; Siracusa , M. ; Salerno , L. ; Russo , F. ; Cagnotto , A. ; Goeganb , M. ; Mennini , T. [1,2,4]Triazole derivatives as 5-HT1A serotonin receptor ligands . Bioorg. Med. Chem. 2002 , 10 , 313 – 323 .
   PubMed Web of Science ®Google Scholar
• Sheldrick , G. M. SHELXS-97 and SHELXL-97: Programs for Crystal Structure Solution and Refinement ; University of Gottingen : Germany , 1997 .
   Google Scholar