Skip to main content

Advertisement

SpringerLink
Log in

Cyanoacetohydrazides in Synthesis of Heterocyclic Compounds

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

Abstract

Use of cyanoacetohydrazides as precursors in reactions leading to construction of heterocycles is reviewed. In addition to some common heterocyclic compounds, synthesis of other uncommon heterocycles such as thiadiazole, oxadiazole, fused heterocycles, and some seven- and eight-membered heterocycles such as benzodiazepine, oxazepine, and benzoxocine starting with cyanoacetohydrazides and their derivatives is also reported. The main aim of this review is to show the application of cyanoacetohydrazides in heterocyclic synthesis via different types of reaction, including cyclocondensation and cyclization. The results are arranged in terms of the type of heterocycle formed, from five-, six-, seven-, to eight-membered and fused rings. This review aims to cover literature up to 2018, showing the distribution of publications involving use of cyanoacetohydrazides for preparation of heterocycles.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Fig. 2
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32
Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Scheme 39
Scheme 40
Scheme 41
Scheme 42
Scheme 43
Scheme 44
Scheme 45
Scheme 46
Scheme 47
Scheme 48
Scheme 49
Scheme 50
Scheme 51
Scheme 52
Scheme 53
Scheme 54
Scheme 55
Scheme 56
Scheme 57
Scheme 58
Scheme 59
Scheme 60
Scheme 61
Scheme 62
Scheme 63
Scheme 64
Scheme 65
Scheme 66
Scheme 67
Scheme 68
Scheme 69
Scheme 70
Scheme 71
Scheme 72
Scheme 73
Scheme 74
Scheme 75
Scheme 76
Scheme 77
Scheme 78
Scheme 79
Scheme 80
Scheme 81
Scheme 82
Scheme 83
Scheme 84
Scheme 85
Fig. 3
Scheme 86
Scheme 87
Fig. 4
Scheme 88
Fig. 5
Fig. 6
Fig. 7
Scheme 89
Fig. 8
Scheme 90

Similar content being viewed by others

References

  1. Martins MAP, Moreira DN, Frizzo CP, Longhi K (2008) J Braz Chem Soc 19:1361–1368

    CAS  Google Scholar 

  2. Khidre RE, Abu-Hashem A, El-Shazly M (2011) Eur J Med Chem 46:5057–5064

    CAS  PubMed  Google Scholar 

  3. Gorolets NY, Yousefi BH, Belaj F, Kappe CO (2004) Tetrahedron 60:8633

    Google Scholar 

  4. Elgemeie GH, Metwally NH (1999) J Chem Res 6:384–385

    Google Scholar 

  5. Mohareb RM, El-Sayed NE, Abdelaziz MA (2012) Molecules 17:8449–8463

    CAS  PubMed  PubMed Central  Google Scholar 

  6. Nilov DB, Granik VG (2006) Russ Chem Bull Int Ed 55:1636–1641

    CAS  Google Scholar 

  7. Amer FAK, Hammouda M, Abdel-Wahab BF (2007) J Chin Chem Soc 54:1543–1552

    CAS  Google Scholar 

  8. Hessein SA (2015) Int J Adv Res 3:654–663

    CAS  Google Scholar 

  9. Abdel-Latif E, Khalil AGM (2014) Res Chem Intermed 30:1551–1557

    Google Scholar 

  10. Elgemeie GH, Metwally NH (1999) J Chem Res 6:384–385

    Google Scholar 

  11. Zelenin KN, Oleinik SV, Alekseev VV, Potekhin AA (2001) Russ J Gen Chem 71:1116–1120

    CAS  Google Scholar 

  12. Al-Said MS, Bashandy MS, Al-qasoumi SI, Ghorab MM (2011) Eur J Med Chem 46:137–141

    CAS  PubMed  Google Scholar 

  13. Ghorab MM, Ragab FA, Heiba HI, El-Gazzar MG (2015) Eur J Med Chem 92:682–692

    CAS  PubMed  Google Scholar 

  14. Desai NC, Shihory NR, Kotadiya GM (2013) Lett Drug Des Discovery 10:632–639

    CAS  Google Scholar 

  15. Ibrahim Badr SM (2011) Turk J Chem 35:131–143

    Google Scholar 

  16. Erian AW, Manhi FM, El-Gohary SZ, AhmedAli F, HilmyElnagdi M (1998) Phosphorus Sulfur Silicon Relat Elem 133:127–139

    CAS  Google Scholar 

  17. Shams HZ, Mohareb RM, Helal MH, Mahmoud AE (2007) Phosphorus Sulfur Silicon Relat Elem 182:237–263

    CAS  Google Scholar 

  18. Allam YA, Nawwar GAM (2002) Heteroat Chem 13:207–210

    CAS  Google Scholar 

  19. Thora VV (2014) IOSR J Appl Chem 7:46–48

    Google Scholar 

  20. Demirbas N, Demirbas A, Sancak K (2002) Turk J Chem 26:801

    CAS  Google Scholar 

  21. Golovko TV, Soloveva NP, Anisimova OS, Granik VG (2003) Chem Heterocycl Compd 39:344

    CAS  Google Scholar 

  22. Girgis AS, Hosni HM, Ahmed-Farag IS (2003) Z Naturforsch 58:678–685

    CAS  Google Scholar 

  23. Elgemeie GH, Elzanate AM (2003) Synth Commun 33:2087–2094

    CAS  Google Scholar 

  24. Mohareb RM, El-Arab EE, El-Sharkawy KA (2009) Sci Pharm 77:355–366

    CAS  Google Scholar 

  25. El-Sayed TA, Ibrahim MA (2010) J Braz Chem Soc 21:1007–1016

    Google Scholar 

  26. Al-Najjar AA, Amer SA, Riad M, Elghamy I, Elnagdi MH (1996) J Chem Res, 296

  27. Li M, Kong W, Wen LR, Liu FH (2012) Tetrahedron 68:4838–4845

    CAS  Google Scholar 

  28. Mahmoud MR, El-Azm FSA (2013) Eur Chem Bull 2:335–340

    CAS  Google Scholar 

  29. Seifi M, Rabori MK, Sheibani H (2013) Mod Res Catal 2:8–12

    CAS  Google Scholar 

  30. Desai NC, Shihory NR, Kotadiya GM, Desai P (2014) Eur J Med Chem 82:480–489

    CAS  PubMed  Google Scholar 

  31. Bondock S, Gieman H (2015) Res Chem Intermed 41:8381–8403

    CAS  Google Scholar 

  32. Elgemeie GH, Elghandour AH, Elzanate AM, AbdElaziz GW (2003) Synth Commun 33:253–258

    CAS  Google Scholar 

  33. Bayat M, Hosseini FS (2017) Tetrahedron Lett 58:1616–1621

    CAS  Google Scholar 

  34. Bayat M, Hosseini FS (2018) J Sulfur Chem 39:279–293

    CAS  Google Scholar 

  35. Elmoghayar MRH, Elagamey AGA, Nasr MYS, Sallam MMM (1885) J Heterocycl Chem 1984:21

    Google Scholar 

  36. Mohareb RM, Abdo NYM (2015) Chem Pharm Bull 63:678–687

    CAS  PubMed  Google Scholar 

  37. Mohareb RM, Ho JZ, Alfarouk FO (2007) J Chin Chem Soc 54:1053–1066

    CAS  Google Scholar 

  38. Nasr T, Bondock S, Youns M (2014) Eur J Med Chem 76:539–548

    CAS  PubMed  Google Scholar 

  39. El-Aal A, Gaber M, El-Gaby MSA, El-Dean AMK, Eyada HA (2004) J Chin Chem Soc 51:1325–1331

    Google Scholar 

  40. El-Rady EA (2006) Synth Commun 36:37–49

    CAS  Google Scholar 

  41. Singh P, Kumar R, Yadav BK, Khanna RS, Tewari AK (2014) RSC Adv 4:51239–51243

    CAS  Google Scholar 

  42. Bayat M, Hosseini H (2017) New J Chem 41:14954–14959

    CAS  Google Scholar 

  43. Elgemeie GEH, El-Ezbawy SR, Ali HA (2001) Synth Commun 31:3459

    CAS  Google Scholar 

  44. Ibrahim NS, Hafez EAA, Mohareb RM (1986) Heterocycles 24:2085

    CAS  Google Scholar 

  45. Rida SM, Habib NS, Badwey EAM, Fahmy HTY, Ghozlan HA (1996) Pharmazie 51:927

    CAS  PubMed  Google Scholar 

  46. Mohareb RM, Samir EM (2012) Open J Med Chem 2:1–9

    CAS  Google Scholar 

  47. Wardakhan WW, El-Sayed NN, Mohareb RM (2013) Acta Pharm 63:45–57

    CAS  PubMed  Google Scholar 

  48. El-Sayed AM (2000) Phosphorus Sulfur Silicon 163:29–40

    CAS  Google Scholar 

  49. Mahmoud MR, El-Ziaty AK, Ismail MF, Shiba SA (2011) Eur J Chem 3:347–355

    Google Scholar 

  50. Ibrahim MA, El-Gohary NM (2015) J Heterocycl Chem 000:1711

    Google Scholar 

  51. Callejo MJ, Lafuente P, Leon NM, Quinteiro M (1990) J Chem Soc Perkin Trans 1:1687–1690

    Google Scholar 

  52. Metwally NH, Abdelrazek FM (2005) Synth Commun 35:2481–2487

    CAS  Google Scholar 

  53. Hadi A (2011) J Kerbala Univ 9:161–181

    Google Scholar 

  54. Kabirifard H, Mashai SE, Hamrahjoo N (2013) Iran J Org Chem 5:1111–1116

    Google Scholar 

  55. Abdelrazek FM, Ghozlan SA, Michael FA (2007) J Heterocycl Chem 44:63–67

    CAS  Google Scholar 

  56. Nápoles M, Peseke K, Quincoces J, Rosado A (2004) Revista CENIC Ciencias Químicas 35:17–21

    Google Scholar 

  57. Jabli D, Dridi K, El Efri ML (2014) Lett Org Chem 11:403–408

    CAS  Google Scholar 

  58. Khodairy A, El-Sayed AM, Salah H, Abdel-Ghany H (2007) Synth Commun 37:3245–3258

    CAS  Google Scholar 

  59. El-Shafie AK, Soliman AM, Sultan AA, Abd-Alla E (2006) J Heterocycl Chem 43:133–137

    CAS  Google Scholar 

  60. Soliman AM, Sultan AA, Ellah OA, El-Shafei AK (2010) Phosphorus Sulfur Silicon Relat Elem 185:1301–1314

    CAS  Google Scholar 

  61. Malicorne G, Bompart J, Giral L, Despaux E (1991) Eur J Med Chem 26:3–11

    CAS  Google Scholar 

  62. Hargreaves SL, Pilkington BL, Russell SE, Worthington PA (2000) Tetrahedron Lett 41:1653–1656

    CAS  Google Scholar 

  63. Szoko E, Tabi T (2010) J Pharm Biomed Anal 53:1180–1192

    PubMed  Google Scholar 

  64. Zhao H, Shi L, Cao JQ, Li W, Wen X, Zhao YQ (2010) Chin Chem Lett 21:1216–1218

    CAS  Google Scholar 

  65. Banik BK, Becker FF (2010) Eur J Med Chem 45:4687–4691

    CAS  PubMed  Google Scholar 

  66. Rodrigues MT, Gomes JC, Smith J, Coelho F (2010) Tetrahedron Lett 51:4988–4990

    CAS  Google Scholar 

  67. Saiki AY, Shen LL, Chen CM, Baranowski J, Lerner CG (1999) Antimicrob Agents Chemother 43:1574–1577

    CAS  PubMed  PubMed Central  Google Scholar 

  68. Cocco MT, Congiu C, Onnis V (2003) Eur J Med Chem 38:37–47

    CAS  PubMed  Google Scholar 

  69. Abadi A, Al-Deeb O, Al-Afify A, El-Kashef H (1999) Farmaco 54:195–201

    CAS  PubMed  Google Scholar 

  70. Ozturk G, Erol DD, Uzbay T, Aytemir MD (2001) Farmaco 56:251–256

    CAS  PubMed  Google Scholar 

  71. Storck P, Aubertin A, Grierson DS (2005) Tetrahedron Lett 46:2919–2922

    CAS  Google Scholar 

  72. Li Q, Mitscher LA, Shen LL (2000) Med Res Rev 20:231–293

    CAS  PubMed  Google Scholar 

  73. Beale JM, Block JH (2010) Organic medicinal and pharmaceutical chemistry. Wolters Kluwer, India

    Google Scholar 

  74. Drews J (2000) Science 287:1960–1964

    CAS  PubMed  Google Scholar 

  75. Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A (2004) Mini Rev Med Chem 4:625–632

    CAS  PubMed  Google Scholar 

  76. Abbate F, Casini A, Owa T, Scozzafava A, Supuran CT (2004) Bioorg Med Chem Lett 14:217–223

    CAS  PubMed  Google Scholar 

  77. Ghorab MM, Alsaid MS, Ceruso M, Nissan YM, Supuran CT (2014) Bioorg Med Chem Lett 14:3684–3695

    Google Scholar 

  78. Bansal Y, Silakari O (2012) Bioorg Med Chem 20:6208–6236

    CAS  PubMed  Google Scholar 

  79. Ansari KF, Lal C (2009) Eur J Med Chem 44:4028–4033

    CAS  PubMed  Google Scholar 

  80. Goker H, Kus C, Boykin DW, Yildiz S, Altanlar N (2002) Bioorg Med Chem Lett 10:2589–2596

    CAS  Google Scholar 

  81. Kazimierczuk Z, Upcroft JA, Upcroft P, Gorska A, Starosciak B, Laudy A (2002) Acta Biochim Pol 49:185–195

    CAS  PubMed  Google Scholar 

  82. Patil A, Ganguly S, Surana S (2008) Rasayan J Chem 1:447–460

    CAS  Google Scholar 

  83. Dubey AK, Sanyal PK (2010) Online J Vet Res 5:63

    Google Scholar 

  84. Naik P, Murumkar P, Giridhar R, Yadav MR (2010) Bioorg Med Chem Lett 18:8418–8456

    CAS  Google Scholar 

  85. Mederski WW, Dorsch D, Anzali S, Gleitz J, Cezanne B, Tsaklakidis C (2004) Bioorg Med Chem Lett 14:3763–3769

    CAS  PubMed  Google Scholar 

  86. Mader M, de Dios A, Shih C, Bonjouklian R, Li T, White W, Uralde BL, Sanchez-Martinez C, Prado M, Jaramillo C (2008) Bioorg Med Chem Lett 18:179–183

    CAS  PubMed  Google Scholar 

  87. Lam T, Hilgers MT, Cunningham ML, Kwan BP, Nelson KJ, Brow-Driver V, Ong V, Trzoss M, Hough G, Shaw KJ, Finn J (2014) J Med Chem 57:651–668

    CAS  PubMed  Google Scholar 

  88. Desai NC, Shihory NR, Kotadiya GM (2014) Chin Chem Lett 25:305–307

    CAS  Google Scholar 

  89. Seenaiah D, Reddy PR, Reddy GM, Padmaja A, Padmavathi V, Krishna NS (2014) Eur J Med Chem 77:1–7

    CAS  PubMed  Google Scholar 

  90. Alp M, Goker H, Brun R, Yildiz S (2009) Eur J Med Chem 44:2002–2008

    CAS  PubMed  Google Scholar 

  91. Andreani A, Granaiola M, Leoni A, Morigi R, Ramballdi M (2001) Eur J Med Chem 36:743–746

    CAS  PubMed  Google Scholar 

  92. Kini SG, Bhat AR, Bryant B, Williamson JS, Dayan FE (2009) Eur J Med Chem 44:492–500

    CAS  PubMed  Google Scholar 

  93. Desai NC, Rajpara KM, Joshi VV (2013) Bioorg Med Chem Lett 23:2714–2717

    CAS  PubMed  Google Scholar 

  94. Belluti F, Fontana G, Dal Bo L, Carenini N, Giommarelli C, Zunino F (2010) Bioorg Med Chem 18:3543–3550

    CAS  PubMed  Google Scholar 

  95. Stefani HA, Gueogjan K, Manarin F, Farsky SHP, Zukerman-Schpector J, Caracelli I, Rodrigues SRP (2012) Eur J Med Chem 58:117–127

    CAS  PubMed  Google Scholar 

  96. Basanagouda M, Shivashankar K, Kulkarni MV, Rasal VP, Patel H, Mutha SS, Mohite AA (2010) Eur J Med Chem 45:1151–1157

    CAS  PubMed  Google Scholar 

  97. Vázquez R, Riveiro ME, Vermeulen M, Alonso E, Mondillo C, Facorro G, Piehl L, Baldi A, Shayo C, Davio C (2010) Bioorg Med Chem 20:5537–5549

    Google Scholar 

  98. Riveiro ME, De Kimpe N, Moglioni A, Monczor F, Shayo C, Davio C (2010) Curr Med Chem 17:1325–1338

    CAS  PubMed  Google Scholar 

  99. Wu XQ, Huang C, Jia YM, Song BA, Li J, Liu XX (2014) Eur J Med Chem 74:717–725

    CAS  PubMed  Google Scholar 

  100. Vianna DR, Hamerski L, Bernardi A, Visentin LC, Pires ENS, Teixeira HF, Salbego CG, Eifler-Lima VL, Battastini AMO, von Poser GL, Pinto AC (2012) Eur J Med Chem 57:268–274

    CAS  PubMed  Google Scholar 

  101. Chen Y, Liu HR, Liu HS, Cheng M, Xia P, Qian K, Wu PC, Lai CY, Xia Y, Yang ZY, Morris-Natschke SL, Lee KH (2012) Eur J Med Chem 49(74e):85

    Google Scholar 

  102. Fong WF, Shen XL, Globisch C, Wiese M, Chen GY, Zhu GY, Yu ZL, Tse AKW, Hu YJ (2008) Bioorg Med Chem 16:3694–3703

    CAS  PubMed  Google Scholar 

  103. Zhou T, Shi Q, Bastow KF, Lee KH (2010) J Med Chem 53:8700–8708

    CAS  PubMed  PubMed Central  Google Scholar 

  104. Karegoudar P, Parasa DJ, Ashok M, Mahalinga M, Poojary B, Holla BS (2008) Eur J Med Chem 43:208–815

    Google Scholar 

  105. Pomarnacka E, Bednarski PJ, Reszka P, Borys ED, Bienczak A, Werel W, Halasa R (2006) Eur J Med Chem 41:633–639

    CAS  PubMed  Google Scholar 

  106. Padmavathi V, Reddy GS, Padmaia A, Kondaiah P, Shazia A (2009) Eur J Med Chem 44:206–2112

    Google Scholar 

  107. Ragavendran JV, Sriram D, Patel SK, Reddy IV, Bharathwajan N, Stables J, Yogeeswari P (2007) Eur J Med Chem 42:146–151

    CAS  PubMed  Google Scholar 

  108. Zora M, Gormen M (2007) J Organomet Chem 692:5026–5032

    CAS  Google Scholar 

  109. Acharya BN, Saraswat D, Kaushik MP (2008) Eur J Med Chem 43:2840–2852

    CAS  PubMed  Google Scholar 

  110. Xia Y, Fan CD, Zhao BX, Zhao J, Shin DS, Miao JY (2008) Eur J Med Chem 43:2347–2353

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran

    Hajar Hosseini & Mohammad Bayat

Authors
  1. Hajar Hosseini
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Bayat
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Bayat.

Ethics declarations

Conflict of Interest

The authors declare no competing financial interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hosseini, H., Bayat, M. Cyanoacetohydrazides in Synthesis of Heterocyclic Compounds. Top Curr Chem (Z) 376, 40 (2018). https://doi.org/10.1007/s41061-018-0218-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-018-0218-z

Keywords

Search

Navigation