A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones

References (124)

1. 1 Taylor, 2014, Supporting Information Rings in Drugs [DOI]
2. 2 Vitaku, 2014, Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals [DOI]
3. 3 Ritchie, 2011, The impact of aromatic ring count on compound developability: Further insights by examining carbo- and hetero-aromatic and -aliphatic ring types [DOI]
4. 4 Cafieri, 1995, Longamide and 3,7-dimethylisoguanine, two novel alkaloids from the marine sponge Agelas longissima [DOI]
5. 5 Uemoto, 1999, Mukanadins A−C, New Bromopyrrole Alkaloids from Marine SpongeAgelasnakamurai [DOI]
6. 6 Cafieri, 1998, Novel Bromopyrrole Alkaloids from the SpongeAgelas dispar [DOI]
7. 7 Mancini, 1997, Hanishin, a Semiracemic, Bioactive C9 Alkaloid of the Axinellid Sponge Acanthella carteri from the Hanish Islands. A Shunt Metabolite? [DOI]
8. 8 Sun, J., Wu, J., An, B., De Voogd, N.J., Cheng, W., and Lin, W. (2018). Bromopyrrole Alkaloids with the Inhibitory Effects against the Biofilm Formation of Gram Negative Bacteria. Mar. Drugs, 16. [DOI]
9. 9 Fattorusso, 2000, Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides [DOI]
10. 10 Tsuda, 2006, Agesamides A and B, Bromopyrrole Alkaloids from SpongeAgelasSpecies: Application of DOSY for Chemical Screening of New Metabolites [DOI]
11. 11 Pettit, 1997, Antineoplastic Agents. 362. Isolation and X-ray Crystal Structure of Dibromophakellstatin from the Indian Ocean SpongePhakellia mauritiana1 [DOI]
12. 12 D’Ambrosio, M., Guerriero, A., Ribes, O., Pusset, J., Leroy, S., and Pietra, F. (1993). Agelastatin a, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the coral sea. J. Chem. Soc. Chem. Commun., 1305–1306. [DOI]
13. 13 Hong, 1998, Agelastatins C and D, New Pentacyclic Bromopyrroles from the SpongeCymbastelasp., and Potent Arthropod Toxicity of (−)-Agelastatin A [DOI]
14. 14 Kinnel, 1993, Palau’amine: A cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge Stylotella agminata [DOI]
15. 15 Rowan, D., Hunt, M.B., and Gaynor, D.L. (1986). Peramine, a novel insect feeding deterrent from ryegrass infected with the endophyte Acremonium loliae. J. Chem. Soc. Chem. Commun., 935–936. [DOI]
16. 16 Jansen, 2014, Nannozinones and Sorazinones, Unprecedented Pyrazinones from Myxobacteria [DOI]
17. 17 Song, 2012, Brevianamides with Antitubercular Potential from a Marine-Derived Isolate of Aspergillus versicolor [DOI]
18. 18 Trigos, 1995, Macrophominol, a diketopiperazine from cultures of Macrophomina phaseolina [DOI]
19. 19 Grube, 2006, Oxocyclostylidol, an Intramolecular Cyclized Oroidin Derivative from the Marine Sponge Stylissacaribica§ [DOI]
20. 20 Han, 2013, Synthesis and Anticancer Activity of All Known (−)-Agelastatin Alkaloids [DOI]
21. 21 Scala, 2010, Bromopyrrole Alkaloids as Lead Compounds against Protozoan Parasites [DOI]
22. 22 Lansdell, 2012, Palau’amine and Related Oroidin Alkaloids Dibromophakellin and Dibromophakellstatin Inhibit the Human 20S Proteasome [DOI]
23. 23 Brimble, 1988, Synthesis of peramine, an insect feeding deterrent mycotoxin from Acremonium lolii [DOI]
24. 24 Mashiko, 2008, An Improved Lanthanum Catalyst System for Asymmetric Amination: Toward a Practical Asymmetric Synthesis of AS-3201 (Ranirestat) [DOI]
25. 25 Meyers, 2007, Novel pyrazolopiperazinone- and pyrrolopiperazinone-based MCH-R1 antagonists [DOI]
26. 26 Fisher, 2007, 8-Hydroxy-3,4-dihydropyrrolo[1,2-a]pyrazine-1(2H)-one HIV-1 integrase inhibitors [DOI]
27. 27 Micheli, 2006, From pyrroles to pyrrolo[1,2-a]pyrazinones: A new class of mGluR1 antagonists [DOI]
28. 28 Ward, 2017, Structure-Guided Discovery of Potent and Selective Inhibitors of ERK1/2 from a Modestly Active and Promiscuous Chemical Start Point [DOI]
29. 29 Casuscelli, 2013, Discovery and optimization of pyrrolo[1,2-a]pyrazinones leads to novel and selective inhibitors of PIM kinases [DOI]
30. 30 Shiokawa, 2016, Discovery of a Novel Scaffold as an Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor Based on the Pyrrolopiperazinone Alkaloid, Longamide B [DOI]
31. 31 Rok, 2018, 6-membered pyrrololactams: An overview of current synthetic approaches to their preparation
32. 32 Bandini, 2007, Versatile Base-Catalyzed Route to Polycyclic Heteroaromatic Compounds by Intramolecular Aza-Michael Addition [DOI]
33. 33 Banwell, 1999, First syntheses of the pyrroloketopiperazine marine natural products (±)-longamide, (±)-longamide B, (±)-longamide B methyl ester and (±)-hanishin [DOI]
34. 34 Papeo, 2005, Total synthesis of (±)-cyclooroidin [DOI]
35. 35 Bandini, 2010, Asymmetric Phase-Transfer-Catalyzed Intramolecular N-Alkylation of Indoles and Pyrroles: A Combined Experimental and Theoretical Investigation [DOI]
36. 36 Ichikawa, 2007, Synthesis of (−)-Agelastatin A by [3.3] Sigmatropic Rearrangement of Allyl Cyanate [DOI]
37. 37 Davis, 2005, Asymmetric Total Synthesis of (−)-Agelastatin A Using Sulfinimine (N-Sulfinyl Imine) Derived Methodologies [DOI]
38. 38 Domostoj, 2004, New Total Synthesis of the Marine Antitumor Alkaloid (−)-Agelastatin A [DOI]
39. 39 Kano, 2012, Stereocontrolled Synthesis of Vicinal Diamines by Organocatalytic Asymmetric Mannich Reaction of N-Protected Aminoacetaldehydes: Formal Synthesis of (−)-Agelastatin A [DOI]
40. 40 Tsuchimochi, 2018, Total synthesis of (−)-agelastatin A: An SH2′ radical azidation strategy [DOI]
41. 41 Dickson, 2009, Total Synthesis of (±)-Agelastatin A, A Potent Inhibitor of Osteopontin-Mediated Neoplastic Transformations [DOI]
42. 42 Hama, 2009, Total Synthesis of (−)-Agelastatin A: The Application of a Sequential Sigmatropic Rearrangement [DOI]
43. 43 Feldman, 2002, Alkynyliodonium Salts in Organic Synthesis. Application to the Total Synthesis of (−)-Agelastatin A and (−)-Agelastatin B [DOI]
44. 44 Feldman, 2002, Alkynyliodonium Salts in Organic Synthesis. Development of a Unified Strategy for the Syntheses of (−)-Agelastatin A and (−)-Agelastatin B [DOI]
45. 45 Reyes, 2012, Bioinspired Total Synthesis of Agelastatin A [DOI]
46. 46 Duspara, 2013, A Short Total Synthesis of the Marine Sponge Pyrrole-2-aminoimidazole Alkaloid (±)-Agelastatin A [DOI]
47. 47 Breckle, 2006, Diels−Alder Reactions of Oroidin and Model Compounds [DOI]
48. 48 Beccalli, 2005, Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: Regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines [DOI]
49. 49 Llauger, 2009, A novel base-mediated intramolecular hydroamination to build fused heteroaryl pyrazinones [DOI]
50. 50 Bhandari, 2011, Diversity-Oriented Approach to Pyrrole-Imidazole Alkaloid Frameworks [DOI]
51. 51 Pescatore, 2010, Identification and SAR of novel pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1) [DOI]
52. 52 Ye, 2016, An Iridium(I) N-Heterocyclic Carbene Complex Catalyzes Asymmetric Intramolecular Allylic Amination Reactions [DOI]
53. 53 Zhuo, 2016, Enantioselective Synthesis of Pyrrole-Fused Piperazine and Piperazinone Derivatives via Ir-Catalyzed Asymmetric Allylic Amination [DOI]
54. 54 Marchais, 1999, Synthesis of the marine carbinolamine (+/−) longamide control of N-1 and C-3 bromopyrrole nucleophilicity [DOI]
55. 55 Sosa, 2000, Controlling cyclizations of 2-pyrrolecarboxamidoacetals. Facile solvation of β-amido aldehydes and revised structure of synthetic homolongamide [DOI]
56. 56 Allmann, 2015, Synthesis of Hydroxypyrrolone Carboxamides Employing Selectfluor [DOI]
57. 57 Jacquot, 2002, Synthesis of the dipyrrolopyrazinone core of dibromophakellstatin and related marine alkaloids [DOI]
58. 58 Chung, 2004, Hypervalent Iodine-Mediated Vicinal Syn Diazidation: Application to the Total Synthesis of (±)-Dibromophakellstatin [DOI]
59. 59 Travert, 2005, Regioselective intramolecular N1–C3 cyclizations on pyrrole–proline to ABC tricycles of dibromophakellin and ugibohlin [DOI]
60. 60 Lindel, 2007, Enantioselective Total Synthesis of (-)-Dibromophakellstatin [DOI]
61. 61 Travert, 2004, A Likely Biogenetic Gateway Linking 2-Aminoimidazolinone Metabolites of Sponges to Proline: Spontaneous Oxidative Conversion of the Pyrrole-Proline-Guanidine Pseudo-peptide to Dispacamide A [DOI]
62. 62 Tian, 2011, Pyrrole-Assisted and Easy Oxidation of Cyclic α-Amino Acid- Derived Diketopiperazines under Mild Conditions [DOI]
63. 63 Ermolenko, 2014, Concise synthesis of Didebromohamacanthin A and Demethylaplysinopsine: Addition of Ethylenediamine and Guanidine Derivatives to the Pyrrole-Amino Acid Diketopiperazines in Oxidative Conditions [DOI]
64. 64 Nelli, 2016, Synthesis of Peramine, an Anti-insect Defensive Alkaloid Produced by Endophytic Fungi of Cool Season Grasses [DOI]
65. 65 Petsi, 2020, 2,5-Diketopiperazine Catalysts as Activators of Dioxygen in Oxidative Processes [DOI]
66. 66 Pandey, 2012, Access to Indole- And Pyrrole-Fused Diketopiperazines via Tandem Ugi-4CR/Intramolecular Cyclization and Its Regioselective Ring-Opening by Intermolecular Transamidation [DOI]
67. 67 Imaoka, 2010, Total Synthesis of (+)-Dibromophakellin and (+)-Dibromophakellstatin [DOI]
68. 68 Imaoka, 2009, Total Synthesis of (+)-Dibromophakellin [DOI]
69. 69 Adams, 2006, A concise synthesis of d,l-brevianamide B via a biomimetically-inspired IMDA construction [DOI]
70. 70 Negoro, 1998, Novel, Highly Potent Aldose Reductase Inhibitors: (R)-(−)-2-(4-Bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine- 4-spiro-3‘-pyrrolidine-1,2‘,3,5‘-tetrone (AS-3201) and Its Congeners [DOI]
71. 71 Zhao, 2016, Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues [DOI]
72. 72 Brimble, 1990, Synthesis of the insect feeding deterrent peramine via Michael addition of a pyrrole anion to a nitroalkene [DOI]
73. 73 Mukherjee, 2010, Asymmetric Total Synthesis ofent-Cyclooroidin [DOI]
74. 74 Kwon, 2015, One-Pot Conversion of Carbohydrates into Pyrrole-2-carbaldehydes as Sustainable Platform Chemicals [DOI]
75. 75 Blackburn, 2014, Histone deacetylase inhibitors derived from 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine and related heterocycles selective for the HDAC6 isoform [DOI]
76. 76 Surase, 2017, Identification and synthesis of novel inhibitors of mycobacterium ATP synthase [DOI]
77. 77 Fukase, 2015, Efficient Synthesis of (–)-Hanishin, (–)-Longamide B, and (–)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates [DOI]
78. 78 Cheng, 2012, Total Syntheses of (−)-Hanishin, (−)-Longmide B, and (−)-Longmide B Methyl Ester via a Novel Preparation of N-Substituted Pyrrole-2-Carboxylates [DOI]
79. 79 Mszar, 2014, NHC–Cu-Catalyzed Addition of Propargylboron Reagents to Phosphinoylimines. Enantioselective Synthesis of Trimethylsilyl-Substituted Homoallenylamides and Application to the Synthesis of S-(−)-Cyclooroidin [DOI]
80. 80 Brimble, 1988, Synthesis of 2-Methylpyrrolo[1,2-a]pyrazin-1(2h)-one [DOI]
81. 81 Yoshimitsu, 2009, Total Synthesis of the β-Catenin Inhibitor, (−)-Agelastatin A: A Second-Generation Approach Based on Radical Aminobromination [DOI]
82. 82 Shigeoka, 2013, Formal synthesis of (−)-agelastatin A: An iron(II)-mediated cyclization strategy [DOI]
83. 83 Voievudskyi, 2015, Synthesis and reactivity of novel pyrrolo[1,2-a]pyrazine derivatives [DOI]
84. 84 Yenice, 2017, Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties [DOI]
85. 85 Cetinkaya, 2014, Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization [DOI]
86. 86 Ito, 2018, A concise synthesis of peramine, a metabolite of endophytic fungi [DOI]
87. 87 Wang, 2004, A Novel Synthesis of Arylpyrrolo[1,2-a]pyrazinone Derivatives [DOI]
88. 88 Dumas, 1988, Total synthesis of peramine [DOI]
89. 89 Ujjinamatada, R.K. (2016). Substituted Tetrahydroquinoline Compounds as ROR Gamma Modulators. (No. 2016/185342 WIPO), WO Patent.
90. 90 Hewitt, 2013, Palladium-catalyzed heteroallylation of unactivated alkenes—Synthesis of citalopram [DOI]
91. 91 Smith, 2018, Catalytic Isohypsic-Redox Sequences for the Rapid Generation of Csp3-Containing Heterocycles [DOI]
92. 92 Boothe, 2017, Synthesis of Substituted γ- and δ-Lactams via Pd-Catalyzed Alkene Carboamination Reactions [DOI]
93. 93 Trost, 2006, New Class of Nucleophiles for Palladium-Catalyzed Asymmetric Allylic Alkylation. Total Synthesis of Agelastatin A [DOI]
94. 94 Anderson, 1998, Studies on Total Synthesis of the Cytotoxic Marine Alkaloid Agelastatin A [DOI]
95. 95 Stien, 1999, Total Synthesis of the Antitumor Marine Sponge Alkaloid Agelastatin A [DOI]
96. 96 Sun, 2007, Total synthesis of rac-longamide B [DOI]
97. 97 Trost, 2009, A Stereodivergent Strategy to Both Product Enantiomers from the Same Enantiomer of a Stereoinducing Catalyst: Agelastatin A [DOI]
98. 98 Dong, 2010, Recent advances in the total synthesis of agelastatins [DOI]
99. 99 Trost, 2010, Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Vinyl Aziridines with Nitrogen Heterocycles: Rapid Access to Biologically Active Pyrroles and Indoles [DOI]
100. 100 Palomba, 2018, A domino approach to pyrazino- indoles and pyrroles using vinyl selenones [DOI]
101. 101 Chizhova, 2018, Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli–Cushman Reaction [DOI]
102. 102 Chizhova, 2020, The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents [DOI]
103. 103 Ilyn, 2005, An efficient synthesis of novel heterocycle-fused derivatives of 1-oxo-1,2,3,4-tetrahydropyrazine using Ugi condensation [DOI]
104. 104 Kounde, 2017, Discovery of 2-oxopiperazine dengue inhibitors by scaffold morphing of a phenotypic high-throughput screening hit [DOI]
105. 105 Imaoka, 2013, Synthetic Approaches to Tetracyclic Pyrrole Imidazole Marine Alkaloids
106. 106 Kovvuri, 2020, Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net (3 + 2) and (4 + 3) Cycloadditions [DOI]
107. 107 Poullennec, 2003, Enantioselective Total Synthesis of (+)-Dibromophakellstatin [DOI]
108. 108 Mayer, 2006, Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation [DOI]
109. 109 Jacquot, 2005, Total Synthesis of the Marine Natural Productrac-Dibromophakellstatin [DOI]
110. 110 Ma, 2015, Syntheses of cyclic guanidine-containing natural products [DOI]
111. 111 Seiple, 2009, Total Synthesis of Palau’amine [DOI]
112. 112 Namba, K., Takeuchi, K., Kaihara, Y., Oda, M., Nakayama, A., Nakayama, A., Yoshida, M., and Tanino, K. (2015). Total synthesis of palau’amine. Nat. Commun., 6. [DOI]
113. 113 Robba, M., Tembo, O.N., Dallemagne, P., and Rault, S. (1993). An Efficient Synthesis of New Phenylpyrrolizine and Phenylpyrrolopyrazine Derivatives. Heterocycles, 36. [DOI]
114. 114 Sandoval, 2018, Two-Step Synthesis of 3,4-Dihydropyrrolopyrazinones from Ketones and Piperazin-2-ones [DOI]
115. 115 Heaney, 2003, α-Keto amides as precursors to heterocycles—generation and cycloaddition reactions of piperazin-5-one nitrones [DOI]
116. 116 Maisto, 2020, Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine [DOI]
117. 117 Piltan, 2013, A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate [DOI]
118. 118 Piltan, 2016, One-Pot, Green and Efficient Synthesis of Pyrrolo[1,2-α]Quinoxalines in Water [DOI]
119. 119 Moradi, 2013, One-pot synthesis of pyrrolo[1,2-a]pyrazines via three component reaction of ethylenediamine, acetylenic esters and nitrostyrene derivatives [DOI]
120. 120 Alizadeh, 2014, An Efficient Approach to the Synthesis of Alkyl 7-Hydroxy-1-oxo-1,2,3,4- tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylates via a One-Pot, Three-Component Reaction [DOI]
121. 121 Piltan, 2014, One-pot synthesis of pyrrolo[1,2-a]quinoxaline and pyrrolo[1,2-a]pyrazine derivatives via the three-component reaction of 1,2-diamines, ethyl pyruvate and α-bromo ketones [DOI]
122. 122 Lessard, 2018, A Photorearrangement To Construct the ABDE Tetracyclic Core of Palau’amine [DOI]
123. 123 Jovanovic, 2019, Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives [DOI]
124. 124 Kostyanovsky, 1997, Unusual reaction of aziridine dimer with acetylene dicarboxylates [DOI]

Cited by 14

Showing 7 of 14 known citations — external sources report more than can currently be individually listed.

Related research

• A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
• Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
• Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
• Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
• Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage