A simple, rapid, expedient and sustainable green strategy for the synthesis of benz-/naphthimidazoles

被引:3
作者
Almansour, Abdulrahman, I [1 ]
Kumar, Raju Suresh [1 ]
Arumugam, Natarajan [1 ]
机构
[1] King Saud Univ, Coll Sci, Dept Chem, POB 2455, Riyadh 11451, Saudi Arabia
关键词
Green chemistry; Arylthioprolines; Benzimidazole; Naphthimidazole; Selectivity; BENZIMIDAZOLE; DERIVATIVES; DESIGN; ACCESS; SAR;
D O I
10.1016/j.jksus.2020.09.001
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
A versatile green chemical procedure for the highly selective construction of 2-aryl substituted benz-/naphthimidazoles starting from the reaction of aromatic 1,2-diamines with a series of substituted arylthioprolines with three to five drops of water under simple grinding at ambient temperature in good yields is described. The short reaction time, simplified experimental procedure, the absence of extraction and chromatographic purification steps in addition to the environment affability makes this green strategy highly attractive in view of green chemistry. The expected reaction to furnish the thiazole grafted benz-/naphthimidazole did not occur. Perhaps the arylthioprolines could be in zwitterionic form, which could react with 1,2-diamine giving dihyrobenzimidazole, which undergoes air oxidation to furnish the 2-aryl benzimidazole rather than the expected thiazole grafted imidazoles. (C) 2020 The Author(s). Published by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码:3153 / 3158
页数:6
相关论文
共 33 条
[1]  
Almansour A.I., 2019, US Patent, Patent No. [US 10,357,485 B1, 10357485]
[2]   Design, synthesis and antiproliferative activity of decarbonyl luotonin analogues [J].
Almansour, Abdulrahman I. ;
Arumugam, Natarajan ;
Kumar, Raju Suresh ;
Mahalingam, S. M. ;
Sau, Samaresh ;
Bianchini, Giulia ;
Carlos Menendez, J. ;
Altaf, Mohammad ;
Ghabbour, Hazem A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 138 :932-941
[3]   Reactivity studies on 4-aminopyrones:: Access to benzimidazole and benzimidazolone derivatives [J].
Amari, M ;
Fodili, M ;
Nedjar-Kolli, B ;
Hoffmann, P ;
Périé, J .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (04) :811-816
[4]   NEW BENZIMIDAZOLE SYNTHESIS [J].
BENINCORI, T ;
SANNICOLO, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) :1029-1033
[5]   Tripeptidyl-peptidase II (TPP II) inhibitory activity of (S)-2,3-dihydro-2-(1H-imidazol-2-yl)-1H-indoles, a systematic SAR evaluation.: Part 2 [J].
Breslin, HJ ;
Miskowski, TA ;
Kukla, MJ ;
De Winter, HL ;
Somers, MVF ;
Roevens, PWM ;
Kavash, RW .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (24) :4467-4471
[6]  
Chi YC, 2000, SYNLETT, P591
[7]   Synthesis of benzimidazoles in high-temperature water [J].
Dudd, LM ;
Venardou, E ;
Garcia-Verdugo, E ;
Licence, P ;
Blake, AJ ;
Wilson, C ;
Poliakoff, M .
GREEN CHEMISTRY, 2003, 5 (02) :187-192
[8]   Focus on new drugs in development against human cytomegalovirus [J].
Emery, VC ;
Hassan-Walker, AF .
DRUGS, 2002, 62 (13) :1853-1858
[9]   METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS [J].
EVANS, BE ;
RITTLE, KE ;
BOCK, MG ;
DIPARDO, RM ;
FREIDINGER, RM ;
WHITTER, WL ;
LUNDELL, GF ;
VEBER, DF ;
ANDERSON, PS ;
CHANG, RSL ;
LOTTI, VJ ;
CERINO, DJ ;
CHEN, TB ;
KLING, PJ ;
KUNKEL, KA ;
SPRINGER, JP ;
HIRSHFIELD, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2235-2246
[10]   A new "traceless" solid-phase synthesis strategy: Synthesis of a benzimidazole library [J].
Huang, WL ;
Scarborough, RM .
TETRAHEDRON LETTERS, 1999, 40 (14) :2665-2668