One-pot preparation of derivatives of the unknown 1,9-diazaphenalene ring by a consecutive electrocyclic ring-closure/Claisen rearrangement/intramolecular amination process

1990 ◽  
pp. 7-8 ◽  
Author(s):  
Pedro Molina ◽  
Mateo Alajarín ◽  
Angel Vidal
Keyword(s):  
Claisen Rearrangement ◽  
Ring Closure ◽  
One Pot ◽  
Derivatives Of

One-pot, Three-component Synthesis of 7H-[1,3,4]Thiadiazolo[ 3,2-a]pyridines from 2-Phenacyl-[1,3,4]thiadiazole Derivatives and Arylmethylene-cyanoacetic Acid Derivatives

2007 ◽  
Vol 62 (10) ◽  
pp. 1298-1304 ◽  
Author(s):  
Imran Ali Hashmi ◽  
Wolfgang Frey ◽  
Ivo C. Ivanovc ◽  
Willi Kantlehner
Keyword(s):  
Ring Closure ◽  
The Novel ◽  
Pyridine Derivatives ◽  
Cyanoacetic Acid ◽  
One Pot ◽  
X Ray ◽  
Thiadiazole Ring ◽  
Thiadiazole Derivatives ◽  
Hydroxy Compounds ◽  
Derivatives Of

Generally, arylmethylene-cyanoacetic acid derivatives react with enols and aromatic or heteroaromatic hydroxy compounds to afford 2-amino-4H-pyran derivatives of type 6. In contrast, a ring closure with the nitrogen atom of the thiadiazole ring occurs when 2-phenacyl-1,3,4-thiadiazoles (1a - d) act on derivatives of arylmethylene-cyanoacetic acid giving rise to the formation of 7H- [1,3,4]thiazolo[3,2-a]pyridine derivatives 5a - r. The same products are obtained if 2-phenacyl-1,3,4- thiadiazoles react with aromatic or heteroaromatic aldehydes and cyanoacetic acid derivatives. The constitution of the novel compounds 5 has been confirmed by an X-ray analysis of 5a.

scholarly journals Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

2015 ◽  
Vol 11 ◽  
pp. 481-492 ◽  
Author(s):  
Alireza Shakoori ◽  
John B Bremner ◽  
Mohammed K Abdel-Hamid ◽  
Anthony C Willis ◽  
Rachada Haritakun ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Heterocyclic System ◽  
The Novel ◽  
Ring Closing Metathesis ◽  
One Pot ◽  
Rapid Access ◽  
Directed Synthesis ◽  
Derivatives Of

Diversity-directed synthesis based on the cascade allylation chemistry of indigo, with its embedded 2,2’-diindolic core, has resulted in rapid access to new examples of the hydroxy-8a,13-dihydroazepino[1,2-a:3,4-b']diindol-14(8H)-one skeleton in up to 51% yield. Additionally a derivative of the novel bridged heterocycle 7,8-dihydro-6H-6,8a-epoxyazepino[1,2-a:3,4-b']diindol-14(13H)-one was produced when the olefin of the allylic substrate was terminally disubstituted. Further optimisation also produced viable one-pot syntheses of derivatives of the spiro(indoline-2,9'-pyrido[1,2-a]indol)-3-one (65%) and pyrido[1,2,3-s,t]indolo[1,2-a]azepino[3,4-b]indol-17-one (72%) heterocyclic systems. Ring-closing metathesis of the N,O-diallylic spiro structure and subsequent Claisen rearrangement gave rise to the new (1R,8aS,17aS)-rel-1,2-dihydro-1-vinyl-8H,17H,9H-benz[2',3']pyrrolizino[1',7a':2,3]pyrido[1,2-a]indole-8,17-(2H,9H)-dione heterocyclic system.

Synthesis of azaanthraquinones: homolytic substitution of pyridines

1982 ◽  
Vol 35 (7) ◽  
pp. 1451 ◽  
Author(s):  
DW Cameron ◽  
KR Deutscher ◽  
GI Feutrill ◽  
DE Hunt
Keyword(s):  
Ring Closure ◽  
Pyridine Derivatives ◽  
Derivatives Of ◽  
Substituted 1 ◽  
Homolytic Substitution

Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6. In particular, derivatives of pyridine-3-carbo-nitrile have been benzoylated at positions 2 and 4. Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1-and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1).

ChemInform Abstract: One-Pot Synthesis of 1-Alkenyl Derivatives of Phospholane and Phosphinane - New Classes of Compounds.

ChemInform ◽  
2010 ◽  
Vol 33 (17) ◽  
pp. no-no
Author(s):  
Graziano Baccolini ◽  
Carla Boga ◽  
Rezio A. Buscaroli
Keyword(s):  
One Pot ◽  
One Pot Synthesis ◽  
Derivatives Of

Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha
Keyword(s):  
Michael Addition ◽  
Aldol Condensation ◽  
Ring Closure ◽  
Dehydration Reaction ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Tandem Process ◽  
First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

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