Intramolecular Diels-Alder Additions of Benzynes to Furans. Exploratory Studies

1986 ◽  
Vol 39 (4) ◽  
pp. 635 ◽  
Author(s):  
WM Best ◽  
D Wege
Keyword(s):  
Carboxylic Acid ◽  
Carbon Atom ◽  
Anthranilic Acid ◽  
Furan Ring ◽  
Alkoxy Group ◽  
Diels Alder ◽  
Ring Systems ◽  
Terminal Carbon Atom ◽  
Furan Moiety

A series of 3-alkoxyanthranilic acids, in which a furan ring is attached to the terminal carbon atom of the alkoxy group, has been prepared. When the chain linking the anthranilic acid and furan ring systems is three or four atoms long, decomposition of the derived diazonium chlorides generates the corresponding benzynes , which are efficiently trapped intramolecularly by the furan moiety. Diazotization of 2-amino-3-furfuryloxybenzoic acid, where the linking chain is two atoms long, results in fragmentation with the formation of 6-diazo-5- oxocyclohexa-1,3-diene-1-carboxylic acid.

Transposition of Aromaticity from a Furan to a Cyclohexane Ring in Furoisoindoles During the Interaction of 3-(Furyl)allylamines with Bromomaleic Anhydride

Synlett ◽  
2020 ◽  
Vol 31 (03) ◽  
pp. 255-260
Author(s):  
Kseniia A. Alekseeva ◽  
Elizaveta A. Kvyatkovskaya ◽  
Eugeniya V. Nikitina ◽  
Vladimir P. Zaytsev ◽  
Svetlana M. Eroshkina ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Furan Ring ◽  
Alder Reaction ◽  
Diels Alder ◽  
Cyclohexane Ring ◽  
Reaction Sequence ◽  
Diels Alder Reaction ◽  
Furan Moiety ◽  
Formation Step

An unexpected four-step reaction sequence was discovered in the course of investigation of the interaction between 3-(furan-2-yl)allylamines and bromomaleic anhydride. This conversion begins with the initial N-acylation of the allylamines by the anhydride, followed by intramolecular Diels–Alder reaction, which is accompanied by a dehydrohalogenation, and ends with the formation of partially unsaturated furo[2,3-f]isoindoles followed by transposition of aromaticity from the furan moiety to the neighboring cyclohexane ring. The reaction between 3-(furan-3-yl)allylamines and bromomaleic anhydride does not stop at a furo[2,3-f]isoindole formation step, but proceeds further with the cleavage of the furan ring in a 100% atom-efficient fashion to provide polysubstituted isoindoline-4-carboxylic acids.

Intramolecular Diels-Alder Additions of Benzynes to Furans. Application to the Total Synthesis of Biflorin, and the Mansonone-E, I and F

1986 ◽  
Vol 39 (4) ◽  
pp. 647 ◽  
Author(s):  
WM Best ◽  
D Wege
Keyword(s):  
Total Synthesis ◽  
Anthranilic Acid ◽  
Diels Alder ◽  
Furan Moiety ◽  
Derivatives Of

Benzynes, generated either by the debromination of an appropriately substituted (o-dibromobenzene, or by the thermolysis of a substituted diazotized anthranilic acid, have been trapped intramolecularly by an attached furan moiety. One such adduct (41) has been transformed into 6,9-dimethylnaphtho[1,8-bc]pyran-3(2H)-one (43), which served as the key intermediate for the total synthesis of the title compounds, all of which are derivatives of 6,9-dimethylnaphtho[1,8-bc]pyran-7,8-quinone.

Synthesis of 3-(6-Azauracil-5-yl)anthranilic Acid and Its Application to the Preparation of Other 1,2,4-Triazine Derivatives

1996 ◽  
Vol 61 (6) ◽  
pp. 941-945 ◽  
Author(s):  
Jan Hlaváč ◽  
Jan Slouka
Keyword(s):  
Carboxylic Acid ◽  
Anthranilic Acid ◽  
Title Compound ◽  
Triazine Derivatives

The title compound was synthesized by alkaline recyclization of isatin-7-carboxylic acid semicarbazone and used for the preparation of 3-oxo-2,3-dihydro-5H-1,2,4-triazino[5,6-b]indol-6-carboxylic acid (8) and 3-oxo-2,3,4,6-tetrahydro-1,2,4-triazino[5,6-c]cinnoline-7-carboxylic acid (9).

Synthesis and properties of a new second-order NLO chromophore containing the benzo[b]furan moiety for electro-optical materials

RSC Advances ◽  
2014 ◽  
Vol 4 (63) ◽  
pp. 33312-33318 ◽  
Author(s):  
Maolin Zhang ◽  
Guowei Deng ◽  
Airui Zhang ◽  
Huajun Xu ◽  
Heyan Huang ◽  
...  
Keyword(s):  
Electron Donor ◽  
Optical Materials ◽  
Furan Ring ◽  
Second Order ◽  
Donor Group ◽  
Nlo Chromophores ◽  
Furan Moiety

We have designed and synthesized a new chromophore having a 1,1,7,7-tetramethyljulolidine fused furan ring as the electron donor group to systematically investigate the role of the benzo[b]furan ring in NLO chromophores.

Synthesis of functionalized isoprenes involving a terminal alkoxy group and their highly regioselective diels-alder reaction

1983 ◽  
Vol 24 (11) ◽  
pp. 1171-1174 ◽  
Author(s):  
Tadakatsu Mandai ◽  
Kazuhito Osaka ◽  
Tadakazu Wada ◽  
Mikio Kawada ◽  
Junzo Otera
Keyword(s):  
Alder Reaction ◽  
Alkoxy Group ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes

2010 ◽  
Vol 6 ◽  
Author(s):  
Priyabrata Roy ◽  
Binay Krishna Ghorai
Keyword(s):  
Diels Alder ◽  
Fischer Carbene Complexes ◽  
One Pot ◽  
Carbene Complexes ◽  
Ring Systems ◽  
First Report ◽  
Fischer Carbene ◽  
Carbonyl Derivatives ◽  
Transient Intermediates ◽  
Three Component Coupling

One-pot three-component coupling ofo-alkynylheteroaryl carbonyl derivatives with Fischer carbene complexes and dienophiles leading to the synthesis of quinoxaline and phenazine ring systems has been investigated. This involves the generation of furo[3,4-b]pyrazine and furo[3,4-b]quinoxaline as transient intermediates, which were trapped with Diels–Alder dienophiles. This is the first report on furo[3,4-b]pyrazine intermediates.

Biomimetic Diels−Alder Cyclizations for the Construction of the Brevianamide, Paraherquamide Sclerotamide, and VM55599 Ring Systems

1998 ◽  
Vol 120 (5) ◽  
pp. 1090-1091 ◽  
Author(s):  
Robert M. Williams ◽  
Juan F. Sanz-Cervera ◽  
Félix Sancenón ◽  
J. Alberto Marco ◽  
Kathleen Halligan
Keyword(s):  
Diels Alder ◽  
Ring Systems

Hydroboration of acyclic allenes with disiamylborane

1969 ◽  
Vol 47 (6) ◽  
pp. 1083-1086 ◽  
Author(s):  
D. S. Sethi ◽  
G. C. Joshi ◽  
D. Devaprabhakara
Keyword(s):  
Carbon Atom ◽  
Transition State ◽  
Steric Effects ◽  
Electrophilic Attack ◽  
Terminal Carbon Atom ◽  
Central Carbon Atom ◽  
Central Carbon

The present investigation demonstrates the hydroboration of 1,2-nonadiene, phenylpropadiene, 3-phenyl-1,2-butadiene, 4,5-nonadiene, and tetramethylallene with disiamylborane. All the allenes except tetramethylallene underwent 100% conversion. Examination of the products indicated preferential electrophilic attack of boron on the least substituted terminal carbon atom in the case of 1,2-nonadiene, phenylpropadiene, 3-phenyl-1,2-butadiene, and on the central carbon atom in 4,5-nonadiene. In tetramethylallene boron, attack was exclusively on the central carbon atom. These results have been explained in terms of steric effects on a four-centered transition state.

Sign in / Sign up

Export Citation Format

Share Document