scholarly journals Regioselective synthesis of benzonitriles via amino-catalyzed [3+3] benzannulation reaction

2020 ◽  
Vol 44 (9-10) ◽  
pp. 592-597
Author(s):  
Lin Jiang ◽  
Wen-Fei Jin ◽  
Liu-Dong Yu ◽  
Ming-Wei Yuan ◽  
Hong-Li Li ◽  
...  

A straightforward synthesis of benzonitriles is achieved via amino-catalyzed [3+3] benzannulation of α,β-unsaturated aldehydes and 4-arylsulfonyl-2-butenenitriles. Using pyrrolidine as an organocatalyst via iminium activation, a series of substituted benzonitriles were obtained in good to high yields in a regioselective manner. This reaction can proceed smoothly under mild reaction conditions and without the aid of any metals, additional oxidants, or strong bases, thus making this an efficient and environmentally friendly method to access benzonitriles.

2019 ◽  
Vol 43 (26) ◽  
pp. 10382-10389 ◽  
Author(s):  
Mahmood Masoudi Khoram ◽  
Davood Nematollahi ◽  
Mahdi Jamshidi ◽  
Hamed Goljani

This research has led to the development of an environmentally friendly method for the synthesis of some new sulfone derivatives with high yields and without using any toxic reagents and solvents.


RSC Advances ◽  
2020 ◽  
Vol 10 (49) ◽  
pp. 29171-29174 ◽  
Author(s):  
Qianfa Jia ◽  
Yunfei Lan ◽  
Xin Ye ◽  
Yinhe Lin ◽  
Qiao Ren

An efficient [4 + 2] benzannulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes was achieved under metal-free reaction conditions selectively delivering a wide range of polyfunctional benzenes in high yields respectively (up to 94% yield).


2015 ◽  
Vol 87 (3) ◽  
pp. 1525-1529 ◽  
Author(s):  
GABRIEL F. RIO ◽  
BÁRBARA V. SILVA ◽  
SABRINA T. MARTINEZ ◽  
ANGELO C. PINTO

This paper describes the preparation of a series of 16 anthranilic acids in yields ranging from 51 to 97%, by treating the isatins with NaOH and H2O2. Independently of the nature of the substituent on the aromatic ring, the reactions were complete in 15 min at room temperature, whereas those of isatins containing a substituent on the nitrogen atom required longer reaction time for completion (45 min) under the same reaction conditions.


2010 ◽  
Vol 65 (4) ◽  
pp. 461-469 ◽  
Author(s):  
Iraj Mohammadpoor-Baltork ◽  
Majid Moghadam ◽  
Shahram Tangestaninejad ◽  
Valiollah Mirkhani ◽  
Zohre Eskandari

An environmentally friendly and highly efficient procedure has been developed for the selective synthesis of 2-aryl-5,6-dihydro-4H-1,3-oxazines and 2-aryl-1,4,5,6-tetrahydropyrimidines by cyclocondensation of arylnitriles with 3-amino-1-propanol and 1,3-diaminopropane in the presence of catalytic amounts of H3PW12O40 under thermal conditions and MW irradiation. Under the same reaction conditions, dicyanobenzenes are transformed to their corresponding mono-oxazines and monotetrahydropyrimidines with excellent chemoselectivity. These reactions are simple and clean, giving the products in high yields and high purity. The catalyst can be easily recovered after the reaction and reused efficiently in subsequent runs.


2017 ◽  
Vol 41 (7) ◽  
pp. 430-433
Author(s):  
Mohammad Hakimi Roknabadi ◽  
Mohammad Hossein Mosslemin ◽  
Razieh Mohebat

A series of 13 aryl indeno[2′,1′:5,6]pyrido[2,3- d]pyrimidine-2,4,6-(3 H,5 H,11 H)-triones, eight of which are new, were synthesised regioselectively in high yields by a three-component reaction of 1,3-indanedione, an araldehyde and 6-aminopyrimidin-2,4(1 H,3 H)-dione in the presence of a deep eutectic solvent comprised of choline chloride/urea (1:2) as the catalyst. The reaction conditions were mild and did not require additional catalysts. Given the inexpensive, nontoxic and recyclable nature of the deep eutectic solvent, these reaction conditions are simple to carry out and environmentally friendly.


RSC Advances ◽  
2014 ◽  
Vol 4 (87) ◽  
pp. 46545-46554 ◽  
Author(s):  
Wen Dai ◽  
Guosong Li ◽  
Lianyue Wang ◽  
Bo Chen ◽  
Sensen Shang ◽  
...  

A facile and environmentally friendly method is presented for the asymmetric oxidation of sulfides with H2O2 by an in situ-formed manganese complex, affording the corresponding chiral sulfoxides in high yields and excellent enantioselectivities.


RSC Advances ◽  
2015 ◽  
Vol 5 (99) ◽  
pp. 81395-81398 ◽  
Author(s):  
Junjie Wu ◽  
Shuanglong Lu ◽  
Danhua Ge ◽  
Hongwei Gu

A highly efficient and environmentally friendly method for the synthesis of tertiary amines by direct interaction of aldehydes with secondary amines was reported over a Pt NWs catalyst under mild reaction conditions.


2015 ◽  
Vol 68 (10) ◽  
pp. 1529 ◽  
Author(s):  
Mehdi Rimaz

Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.


2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.


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