Non-Isocyanide-Based Three-Component Reactions: From Strecker to Nowadays

被引:0
作者
Morales-Salazar, Ivette [1 ]
Bouillon, Jean-Philippe [2 ]
Gonzalez-Zamora, Eduardo [1 ]
Islas-Jacome, Alejandro [1 ]
机构
[1] Univ Autonoma Metropolitana Iztapalapa, Dept Quim, Ave Ferrocarril San Rafael Atlixco 186,Col Leyes R, Mexico City 09310, Mexico
[2] Normandie Univ, Univ Rouen Normandie, CNRS, COBRA UMR 6014,INC3M FR 3038,INSA Rouen Normandie, F-76000 Rouen, France
关键词
MCRs; isocyanides; multicomponent reactions; DFT-based calculations; reaction mechanisms; STEREOSELECTIVE TOTAL-SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; WILLGERODT-KINDLER REACTION; KABACHNIK-FIELDS REACTION; CRYSTAL-STRUCTURE ANALYSIS; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; MANNICH REACTION; STEREOCONTROLLED SYNTHESIS;
D O I
10.29356/jmcs.v69i1.2301
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Almost two centuries have passed since Strecker synthesized for the first time the alpha-aminoacid DLalanine via a sequential combination of acetaldehyde with aqueous ammonia and hydrogen cyanide, coupled to a further hydrolysis of the resulting alpha-aminonitrile using an acid aqueous solution. Since then, a broad variety of high valued products in various fields of science and technology have been synthesized via three-component reactions (3CRs) or via one-pot methodologies involving 3CRs coupled smartly to further processes like functionalizations, condensations, cross couplings, cyclizations, ring openings, and so on. In the same way, very interesting and useful computational calculations behind understanding reaction mechanisms related to 3CRs, conformational analyses, and energy profiles have been performed. All these topics are on the scope of the present review, which covers selected and elegant based 3CRs (except for the Ugi-3CR or its variants), and other unclassified 3CR-based works from 2010 to nowadays.
引用
收藏
页码:185 / 258
页数:74
相关论文
共 151 条
  • [1] Double "Open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds
    Abe, Takumi
    Shimizu, Haruka
    Takada, Shiori
    Tanaka, Takahiro
    Yoshikawa, Mai
    Yamada, Koji
    [J]. ORGANIC LETTERS, 2018, 20 (06) : 1589 - 1592
  • [2] Novel thieno[2,3-d]pyrimidines: their design, synthesis, crystal structure analysis and pharmacological evaluation
    Adepu, Raju
    Rambabu, D.
    Prasad, Bagineni
    Meda, Chandana Lakshmi T.
    Kandale, Ajit
    Krishna, G. Rama
    Reddy, C. Malla
    Chennuru, Lakshmi N.
    Parsa, Kishore V. L.
    Pal, Manojit
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (29) : 5554 - 5569
  • [3] New promising generation of phosphates α-aminophosphonates: Design, synthesis, in-vitro biological evaluation and computational study
    Aissa, Rim
    Guezane-Lakoud, Samia
    Gali, Lynda
    Toffano, Martial
    Ignaczak, Anna
    Adamiak, Marta
    Merabet-Khelassi, Mounia
    Guillot, Regis
    Aribi-Zouioueche, Louisa
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2022, 1247
  • [4] Combined Role of the Asymmetric Counteranion-Directed Catalysis (ACDC) and Ionic Liquid Effect for the Enantioselective Biginelli Multicomponent Reaction
    Alvim, Haline G. O.
    Pinheiro, Danielle L. J.
    Carvalho-Silva, Valter H.
    Fioramonte, Mariana
    Gozzo, Fabio C.
    da Silva, Wender A.
    Amarante, Giovanni W.
    Neto, Brenno A. D.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19) : 12143 - 12153
  • [5] A convenient approach towards 2-and 3-aminobenzo[b]thiophenes
    Androsov, Dmitry A.
    Solovyev, Andrey Y.
    Petrov, Mikhail L.
    Butcher, Ray J.
    Jasinski, Jerry P.
    [J]. TETRAHEDRON, 2010, 66 (13) : 2474 - 2485
  • [6] [Anonymous], 2005, Strategic Applications of Named Reactions in Organic Synthesis
  • [7] Modular Synthesis of Dipyrroloquinolines: A Combined Synthetic and Mechanistic Study
    Appun, Johannes
    Stolz, Ferdinand
    Naumov, Sergej
    Abel, Bernd
    Schneider, Christoph
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) : 1737 - 1744
  • [8] Ayaz M., 2013, Sci. synthesis: multicomponent react, V1, P99
  • [9] Synthesis of 2-julolidin-imidazo[1,2-a]pyridines via Groebke-Blackburn-Bienayme reaction and studies of optical properties
    Basavanag, Unnamatla M. V.
    Islas-Jacome, Alejandro
    Renteria-Gomez, Angel
    Conejo, Alain S.
    Kurva, Mahanandaiah
    Jimenez-Halla, J. Oscar C.
    Velusamy, Jayaramakrishnan
    Ramos-Ortiz, Gabriel
    Gamez-Montano, Rocio
    [J]. NEW JOURNAL OF CHEMISTRY, 2017, 41 (09) : 3450 - 3459
  • [10] 3-Imino derivative-sulfahydantoins: Synthesis, in vitro antibacterial and cytotoxic activities and their DNA interactions
    Baskan, Ceren
    Erturk, Aliye Gediz
    Aydin, Birsen
    Siriken, Belgin
    [J]. BIOORGANIC CHEMISTRY, 2022, 119