Efficient and High-Yielding Protocol for the Synthesis of Nitriles from Aldehydes

REFERENCES

• Tennant , G. In Comprehensive Organic Chemistry ; D. Barton , D. W. Ollis , I. O. Sutherland (Eds.); Pergamon Press : Oxford , 1979 ; vol. 2 , p. 528 .
   Google Scholar
• (a) Lai , G. ; Bhamare , N. K. ; Anderson , W. K. A one-pot method for the efficient preparation of aromatic nitriles from aldehydes using ammonia, magnesium sulfate, and manganese dioxide . Synlett 2001 , 230 – 231 ; (b) Janakiraman , M. N. ; Watenpaugh , K. D. ; Tomich , P. K. ; Chong , K. T. ; Turner , S. R. ; Tommasi , R. A. ; Thaisrivongs , S. ; Strohbach , J. W. Non-peptidic HIV protease inhibitors: C2-symmetry-based design of bis-sulfonamide dihydropyrones . Bioorg. Med. Chem. Lett. 1998 , 8 , 1237 – 1242 .
   Google Scholar
• (a) Gu , X.-H. ; Wan , X.-Z. ; Jiang , B. Syntheses and biological activities of bis(3-indolyl)thiazoles, analogues of marine bis(indole)alkaloid nortopsentins . Bioorg. Med. Chem. Lett. 1999 , 9 , 569 – 572 ; (b) Chihiro , M. ; Nagamoto , H. ; Tekemura , I. ; Kitano , K. ; Komatsu , H. ; Sekiguchi , K. ; Tabusa , F. ; Mori , T. ; Tominaga , M. ; Yabuuchi , Y. Novel thiazole derivatives as inhibitors of superoxide production by human neutrophils: Synthesis and structure–activity relationships . J. Med. Chem. 1995 , 38 , 353 – 358 .
   PubMed Web of Science ®Google Scholar
• Jnaneshwara , G. K. ; Deshpande , V. H. ; Lalithambika , M. ; Ravindranathan , T. ; Bedekar , A. V. Natural kaolinitic clay–catalyzed conversion of nitriles to 2-oxazolines . Tetrahedron Lett. 1998 , 39 ( 5–6 ), 459 – 462 .
   Web of Science ®Google Scholar
• (a) Wittenberger , S. J. ; Donner , B. G. Dialkyltin oxide–mediated addition of trimethylsilyl azide to nitriles: A novel preparation of 5-substituted tetrazols . J. Org. Chem. 1993 , 58 , 4139 – 4141 ; (b) Bailey , T. R. ; Diana , G. D. ; Kowalczyk , P. J. ; Akullian , V. ; Eissenstat , M. A. ; Cutcliffe , D. ; Mallamo , J. P. ; Carabateas , P. ; Pevear , D. C. Antirhinoviral activity of heterocyclic analogs of Win 54954 . J. Med. Chem. 1992 , 35 , 4628 – 4633 ; (c) Kadaba , P. K. Role of protic and dipolar aprotic solvents in heterocyclic syntheses via 1,3-dipolar cycloaddition reactions . Synthesis 1973 , 6 , 71 – 84 .
   Web of Science ®Google Scholar
• (a) Moody , C. J. ; Doyle , K. J. Chapter 1: The synthesis of oxazoles from diazocarbonyl compounds . Prog. Heterocyclic Chem. 1997 , 9 , 1 – 16 ; (b) Ducept , P. C. ; Marsden , S. P. Synthesis and reactivity of 4-silylated oxazoles . Synlett 2000 , 5 , 692 – 694 .
   Google Scholar
• Fabiani , M. E. Angiotensin receptor subtypes: Novel targets for cardiovascular therapy . Drug News Perspect. 1999 , 12 , 207 – 215 .
   Web of Science ®Google Scholar
• Anastas , P. T. ; Warner , J. C. Green Chemistry: Theory and Practice ; Oxford University Press : Oxford , 1998 ; (b) Clark , J. H. Catalysis for green chemistry. Pure Appl. Chem. 2001, 73 , 103 – 111 .
   Google Scholar
• Mowry , D. T. The preparation of nitriles . Chem. Rev. 1948 , 42 , 189 – 283 .
   PubMed Web of Science ®Google Scholar
• (a) Semmelhack , M. F. ; Schmid , C. R. Nitroxyl-mediated electro-oxidation of amines to nitriles and carbonyl compounds . J. Am. Chem. Soc. 1983 , 105 , 6732 – 6734 ; (b) Chen , F. E. ; Kuang , Y. Y. ; Dai , H. F. ; Lu , L. ; Huo , M. A. Selective and mild oxidation of primary amines to nitriles with trichloroisocyanuric acid . Synthesis 2003 , 17 , 2629 – 2631 .
   Web of Science ®Google Scholar
• (a) Baxendale , I. R. ; Ley , S. V. ; Sneddon , F. H. A clean conversion of aldehydes to nitriles using a solid-supported hydrazine. Synlett 2002, 5, 775–777; (b) Kuo , C. W. ; Zhu , J. L. ; Wu , J. D. ; Chu , C. M. ; Yao , C. F. ; Shia , K. S. A convenient new procedure for converting primary amides into nitriles. Chem. Commun. 2007, 301–303; (c) Phillips , B. A. ; Fodor , G. ; Gal , J. ; Letourneau , F. ; Ryan , J. J. Mechanism of the von Braun amide degradations with carbonyl bromide or phosphorus penta bromide. Tetrahedron 1973, 29, 3309–3327.
   Web of Science ®Google Scholar
• Lee , J. C. ; Yoon , J. M. ; Baek , J. W. A novel and efficient synthesis of nitriles from aldehydes under solvent-free microwave irradiation conditions . Bull. Korean Chem. Soc. 2007 , 28 , 29 – 30 .
   Google Scholar
• Talukdar , S. ; Hsu , J. ; Chou , T. ; Fang , J. Direct transformation of aldehydes to nitriles using iodine in ammonia water . Tetrahedran Lett. 2001 , 42 , 1103 .
   Web of Science ®Google Scholar
• Suzuki , H. ; Nakaya , C. A convenient one-step method of converting electron-rich aromatic aldehydes into nitriles . synthesis 1992 , 7 , 641 – 642 .
   Google Scholar
• Digambar , D. G. ; Sameer , V. R. ; Babasaheb , V. K. ; Shisodia , S. U. ; Ravikumar , M. B. ; Praveen , S. S. ; Sunil , S. C. ; Rajendra , P. P. Facile synthesis of nitriles from aromatic aldehydes using DMSO-I2 . Synth. Commun. 2007 , 37 , 257 – 259 .
   Google Scholar
• (a) Pasha , M. A. ; Madhusudana Reddy , M. B. An efficient method of synthesis of N, N′-disubstituted ureas/thioureas by a zinc chloride–catalyzed thermal reaction . Synth. Commun. 2009 , 39 , 2928 – 2934 ; (b) Pasha , M. A. ; Jayashankara , V. P. Molecular iodine–catalyzed synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent–free condition . Bioorg. Med. Chem. Lett. 2007 , 17 , 621 – 623 ; (c) Pasha , M. A. ; Jayashankara , V. P. ; Swamy , N. R. A simple and efficient procedure for the one–pot synthesis of β-acetamido-β-aryl-propiophenones by molecular iodine catalyzed tandem reaction . Synth. Commun. 2007 , 37 , 1551 – 1556 ; (d) Manjula , K. ; Pasha , M. A. Rapid method of converting primary amides to nitriles and nitriles to primary amides by ZnCl2 using microwaves under different reaction conditions . Synth. Commun. 2007 , 37 , 1545 – 1550 ; (e) Pasha , M. A. ; Nizam , A. ZnCl2-catalysed expeditious route to nitriles . Synth. Commun. 2010 , 40 , 1276 – 1279 .
   Web of Science ®Google Scholar
• Caddick , S. ; Fitzmaurice , R. Microwave-enhanced synthesis . Tetrahedron 2009 , 65 ( 17 ), 3325 – 3355 .
   Web of Science ®Google Scholar