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Molecules, Volume 2, Issue 4 (April 1997) – 11 articles , Pages 62-79, Articles M1-M9

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48 KiB  
Article
Synthesis and Reactions of Furo[2,3-b]pyrroles
by A. Krutosiková, C. A. Ramsden, M. Dandárová and A. Lycka
Molecules 1997, 2(4), 69-79; https://0-doi-org.brum.beds.ac.uk/10.3390/20400069 - 20 Apr 1997
Cited by 16 | Viewed by 10336
Abstract
Methyl 6H-furo[2,3-b]pyrrole-5-carboxylate (2a) was prepared by thermolysis of the corresponding methyl 2-azido-3-(3-furyl)propenoate (1). 6-Methyl (2b) and 6-benzyl (2c) derivatives were obtained using phase-transfer catalysis conditions (PTC). The formylation of 2a-2c gave 2-formylated compounds (3a-3c). Compounds 4b, 4c were prepared by reactions [...] Read more.
Methyl 6H-furo[2,3-b]pyrrole-5-carboxylate (2a) was prepared by thermolysis of the corresponding methyl 2-azido-3-(3-furyl)propenoate (1). 6-Methyl (2b) and 6-benzyl (2c) derivatives were obtained using phase-transfer catalysis conditions (PTC). The formylation of 2a-2c gave 2-formylated compounds (3a-3c). Compounds 4b, 4c were prepared by reactions of corresponding esters 2b, 2c with hydrazine in refluxing ethanol. By reaction of 3a-3c with hydroxylammonium chloride in acetic anhydride in the presence of pyridine, methyl 2-cyano-6-R1-furo[2,3-b]pyrrole-5-carboxylates (5a-5c) were obtained. The reaction of these compounds with sodium azide and ammonium chloride in dimethylformamide led to methyl 2-(5'-tetrazolyl)-6-R1-furo[2,3-b]pyrrole-5-carboxylates (6a-6c). A series of 5-methoxycarbonyl-6-R1-furo[2,3-b]pyrrole-2-carbaldehyde N,N-dimethylhydrazones (7a-7c) was prepared from methyl 2-formyl-6-R1-furo[2,3-b]pyrrole-5-carboxylates (3a-3c) and unsym-dimethylhydrazine. The correlation of the 13C and 15N chemical shifts with the data of the calculated (AM1) net atomic charges is discussed. Full article
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81 KiB  
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1-Ethyl 4-(2-oxopropyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate
by Jin-Cong Zhuo and Hugo Wyler
Molecules 1997, 2(4), M9; https://0-doi-org.brum.beds.ac.uk/10.3390/M9 - 15 Apr 1997
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(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
81 KiB  
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1-Ethyl 4-(1,1-dimethylethyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate
by Jin-Cong Zhuo and Hugo Wyler
Molecules 1997, 2(4), M8; https://0-doi-org.brum.beds.ac.uk/10.3390/M8 - 15 Apr 1997
Cited by 1 | Viewed by 3157
Abstract
The diester 2 was prepared by the addition of tert-butanol to 1 according to the reported procedure [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
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81 KiB  
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1-Ethyl 4-(1-methylethyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate
by Jin-Cong Zhuo and Hugo Wyler
Molecules 1997, 2(4), M7; https://0-doi-org.brum.beds.ac.uk/10.3390/M7 - 15 Apr 1997
Viewed by 3211
Abstract
The diester 2 was prepared by the addition of iso-propanol to 1 according to the reported procedure [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
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81 KiB  
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1-Ethyl 4-propyl 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate
by Jin-Cong Zhuo and Hugo Wyler
Molecules 1997, 2(4), M6; https://0-doi-org.brum.beds.ac.uk/10.3390/M6 - 15 Apr 1997
Cited by 12 | Viewed by 3283
Abstract
The diester 2 was prepared by the addition of propanol to 1 according to the reported procedure [1] [...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
81 KiB  
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1-Ethyl 4-(2-methoxyethyl) 2-(1,2,3,4-Tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)butanedioate
by Jin-Cong Zhuo and Hugo Wyler
Molecules 1997, 2(4), M5; https://0-doi-org.brum.beds.ac.uk/10.3390/M5 - 15 Apr 1997
Cited by 21 | Viewed by 3198
Abstract
The diester 2 was prepared by the addition of 2-methoxyethanol to 1 according to the reported procedure [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
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Scheme 1

82 KiB  
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N-(3,4-Dichlorophenyl)methyl Oxamic Acid
by Shu-Kun Lin
Molecules 1997, 2(4), M4; https://0-doi-org.brum.beds.ac.uk/10.3390/M4 - 15 Apr 1997
Cited by 12 | Viewed by 3370
Abstract
A mixture of N-(3,4-dichlorophenyl)methyl oxamic acid ethyl ester [1] (7.609 g, 27.56 mmol), ethanol (400 ml), NaOH (1N, 32 ml) and water (200ml) was stirred at r.t. overnight under N2.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
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Scheme 1

83 KiB  
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N,N'-bis[(3,4-Dichlorophenyl)methyl]ethanediamide
by
Molecules 1997, 2(4), M3; https://0-doi-org.brum.beds.ac.uk/10.3390/M3 - 15 Apr 1997
Viewed by 3296
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
81 KiB  
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Propyl 3-(1,2,3,4-Tetrahydro-1,3,6-trimethyl-2,4-dioxopyrimidin-5-yl)butanoate
by Jin-Cong Zhuo and Hugo Wyler
Molecules 1997, 2(4), M10; https://0-doi-org.brum.beds.ac.uk/10.3390/M10 - 15 Apr 1997
Viewed by 3099
Abstract
The compound 2 was prepared by the addition of propanol to 1 according to the reported procedure [1].[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
80 KiB  
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1,3-Di(4-benzyloxybenzoyl)indole
by Shu-Kun Lin
Molecules 1997, 2(4), M1; https://0-doi-org.brum.beds.ac.uk/10.3390/M1 - 15 Apr 1997
Cited by 1 | Viewed by 4127
Abstract
The general part of the experimental section [1] has been presented elsewhere.[...] Full article
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
38 KiB  
Article
o-Nitroaryl-bis(5-methylfur-2-yl)methanes as Versatile Synthons for the Synthesis of Nitrogen-Containing Heterocycles
by Alexander V. Butin, Vladimir T. Abaev, Tat’yana A. Stroganova and Andrey V. Gutnov
Molecules 1997, 2(4), 62-68; https://0-doi-org.brum.beds.ac.uk/10.3390/20400062 - 10 Apr 1997
Cited by 30 | Viewed by 8521
Abstract
2-Nitroaryldifurylmethanes 1a and 1b, readily available by condensation of 2-nitrobenzaldehyde and 6-nitroveratraldehyde with 2-methylfuran, were transformed into indole, cinnoline and benzothiazine-3,1 derivatives. The reduction of 2-nitroaryldifurylmethanes gave the corresponding anilines 2a,b or indole 3 depending on the reaction conditions. A plausible mechanism for [...] Read more.
2-Nitroaryldifurylmethanes 1a and 1b, readily available by condensation of 2-nitrobenzaldehyde and 6-nitroveratraldehyde with 2-methylfuran, were transformed into indole, cinnoline and benzothiazine-3,1 derivatives. The reduction of 2-nitroaryldifurylmethanes gave the corresponding anilines 2a,b or indole 3 depending on the reaction conditions. A plausible mechanism for the last reaction involving intramolecular heterocyclic addition between a nitroso-group and a furan ring is proposed. Diazotisation of the amine 2b gave a cinnoline derivative - a product of intramolecular oxidative furan ring opening. Treatment of isothiocyanates 7a,b with perchloric acid resulted in a new rearrangement with furan ring migration leading to the 4-Hbenzothiazine-3,1 derivatives. Full article
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Scheme 1

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