Catalyst-Free Chemoselective Synthesis of 3,4-Dihydroquinazoline-2-thiones and 2-Imino[1,3]benzothiazines

Xie, Ting; Xiao, Yu; Zhao, Shuai; Hu, Xiu‐Qin; Xu, Peng‐Fei

doi:10.1021/acs.joc.6b01232

Cited by 28 publications

(8 citation statements)

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“…Fukamachi et al (2010) described a selective construction of 3,4-dihydroquinazoline-2-thiones by reacting 3-(2-isothiocyanatophenyl)propanoic derivatives with primary amines. 3,4-Dihydroquinazoline-2-thiones can also be synthesized from isothiocyanates with 2-aminophenyl acrylates or 2-amino chalcones (Hua et al, 2014; Xie et al, 2016). However, there are very few reports on the production of 4-alkenylquinazolinones and 4-alkenylquinazolinthiones.…”

Section: Introductionmentioning

confidence: 99%

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

et al. 2019

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A new series of 3-substituted 4-methylene-quinazolinthiones and 4-methylene-quinazolinones were synthesized in moderate to excellent yield through a simple reaction of 2-aminoacetophenones with isocyanates or isothiocyanates. The reaction shows good tolerance of many important functional groups in the presence of air and water under metal-free conditions. Only water is produced as a coproduct, rendering this “green” methodology a highly versatile and eco-friendly alternative to the existing methods for the construction of the quinazolinone/quinazolinthione framework. We have interpreted the reaction mechanism by use of quantum chemical calculations on the basis of state-of-the-art computational methods SMD-B3LYP-D3(BJ)/BS1//B3LYP/BS1.

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Section: Introductionmentioning

confidence: 99%

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

et al. 2019

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“…Chemodivergent syntheses are of great value for obtaining skeletal divergence in organic and medicinal chemistry . Over the past few decades, chemoselective control achieved utilizing metal catalysts and solvents has received increasing attention, while relatively few papers have described temperature‐dependent reactions . However, since being first discovered by Woodward and Baer in 1944, kinetic and thermodynamic control of reactions have remained as important topics in organic synthesis for enhancing reaction efficiency and for increasing molecular diversity.…”

Section: Methodsmentioning

confidence: 99%

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Zhou

Jia

et al. 2017

Asian J Org Chem

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“…Apart from 1,3-thiazinones, the Xu and Hu group recently demonstrated the chemoselective syntheseso f2 -imino-[1,3]benzothiazines 15 and 3,4-dihydroquinazoline-2-thiones 16 by using ortho-aminocinnamates 13 and isothiocyanates 14 without any catalyst through modulation of the solvents ystem (Scheme 80). [118] 2-Imino-[1,3]-benzothiazines 15 were obtained from at hia-Michael addition reaction in CH 2 Cl 2 in moderate-toexcellent yields, whilst 3,4-dihydroquinazoline-2-thiones 16 were obtained from an aza-Michael addition reaction in DMSO in excellent yields within av ery short reactiont ime. During their investigation, several solvents, including DCE, CH 2 Cl 2 , DMSO,T HF,M eOH,t oluene,1 ,4-dioxane, MeCN, andw ater, were examined and the thia-Michael product was obtained as the sole product in CH 2 Cl 2 at 40 8C.…”

Section: Catalyst-free Thia-michael Addition Reactionsmentioning

confidence: 99%

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

2018

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The thia-Michael addition reactionh as been demonstrated to be ah ighly powerful tool in organic synthesis. Indeed, the influential natureo ft his reactionh as been wellestablished in the fields of medicinal chemistry,c atalysis, drug discovery,a nd materials science. The emergence of numerous synthetic strategies that take advantage of thia-Michael addition reactions of electron-deficienta lkenes has unleashed countless opportunities for the design and synthesis of diverse biologically relevant organosulfurc ompounds. However,d espite myriad potential synthetic applications, there has not been anye xclusive reviewso ft he thia-Michael addition reaction. Therefore, this Focus Review plots the journeyo ft he thia-Michael addition reaction in organic synthesis, and is categorized according to catalyzed and catalyst-free thia-Michael addition reactions. Figure 1. Summary of the applicationsoft hia-Michael adducts.[a] Dr.Scheme1.Catalyzed pathways for the thia-Michael addition reaction.EW-G = electron-withdrawing group.Scheme2.Acetic-acid-catalyzed thia-Michael additionr eaction proposed by Allen et al. [24] AsianJ.O rg.Scheme3.Indium-bromide-catalyzed thia-Michael addition reaction.Scheme4.Thia-Michael addition reaction followed by a1 ,2-addition of TMSCN in one pot. TMSCN = trimethylsilyl cyanide.Scheme5.Bi III -catalyzedt hia-Michael additionreactiono fa,b-unsaturated carbonyl compounds. Tf = trifluoromethanesulfonyl.Scheme6.Bismuth-triflate-catalyzed synthesis of bis-thioether compounds. Bn = benzyl.Scheme7.Iron-/copper-catalyzed thia-Michael additionr eaction.Scheme8.VO(OTf) 2 -mediated synthesis of b-mercapto ketones. Np = naphthyl.Scheme9.Substrate scope for the synthesis of 3-sulfanyl-substituted 1-(arylamino)-pyrrolidine-2,5-diones.Scheme10. Regio-and enantioselective addition at the d position of conjugated systems.Scheme11. Mechanistic modelf or the enantioselective d addition of at hiol to an a,b,g,d-unsaturated dienone,catalyzed by achiral Fe III Àsalenc omplex.Scheme12. Chemoselectivesynthesis of 2-amino-3,1-benzothiazines (15) and 3,4-dihydroquinazoline-2-thiones (16)byu sing ortho-aminocinnamate (13)a nd isothiocyanates 14.Scheme13. Reactionmechanism for the chemoselective synthesis of 2amino-3,1-benzothiazines (15)and 3,4-dihydroquinazoline-2-thiones (16).Scheme14. ZrCl 4 -assisted three-component reactionf or the synthesiso fbaryl-b-mercapto ketones.Scheme15. LiF-nanocube-mediated thia-Michael addition reaction.Scheme57. Ni II -catalyzed enantioselective synthesiso f2-aryl-3-nitrothiochroman-4-ols.Scheme58. Te ntative reaction mechanism for the Ni II -catalyzed asymmetric synthesis of 2-aryl-3-nitrothiochroman-4-ols.Scheme59. Pepsin-catalyzed synthesis of functionalized chiral dihydrothiophenes.Scheme69. Mechanistic aspects of the stereoselectives ynthesis of tetrahydrothioxanthenones.Scheme70. Enantioselectivesynthesis of methyl 2-((R)-2-nitro-1-(aryl/heteroaryl)ethylthio)acetatesa nd thiomorpholin-3-ones.Scheme71. Water-accelerated thia-Michael additionr eaction proposedb y Chakraborti and co-work...

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Catalyst-Free Chemoselective Synthesis of 3,4-Dihydroquinazoline-2-thiones and 2-Imino[1,3]benzothiazines

Cited by 28 publications

References 65 publications

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

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