Tri- and Tetracyclic Azepine Derivatives by Thermally Induced Cyclization of Aminoallenes and Semicyclic 2-Dienamines

Reinhard, R.; Glaser, M.; Neumann, and Ralf; Maas, Gerhard

doi:10.1021/jo9710036

Cited by 40 publications

(15 citation statements)

References 24 publications

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“…Deuterium labeling studies by these authors indicated that the key stage was intramolecular migration of hydride ion. The aminoallenes 133 could also cyclize to azepines 134 when heated [96]. In the reaction of allene 135 with dimethyl acetylenedicarboxylate, the initially formed cyclobutenes 136 rearranged to the condensed rings 137, forming a new C-C bond at the α-carbon atom of the tertiary amine [97].…”

Section: -92%mentioning

confidence: 99%

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Platonova

Глухарева

Zimovets

et al. 2013

Chem Heterocycl Comp

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The term "tert-amino effect" was proposed in 1972 [1] for the cyclization reactions of tertiary anilines containing various double bonds at the ortho position. Meth-Cohn and Suschitzky [1] referred to the first observation of the tert-amino effect by Pinnow in 1895 [2]. Many different examples of reactions involving the tert-amino effect have now accumulated, and it clearly is a convenient method for the synthesis of an impressive number of nitrogen-containing heterocycles that otherwise might be difficult to obtain. Reviews were published by Reinhoudt in 1990 [3] and by Meth-Cohn in 1996 [4] on heterocyclization reactions that take place by the mechanism of the tert-amino effect. Another review dedicated to 1,6-and 1,8-naphthiridine derivatives was published in 2003 by Quintela [5]. In the review [6] that we published in 2005, attention was focused on the use of such reactions for the synthesis of spiro compounds. In the review [7], published in 2006, the cyclization reactions of ortho-vinylanilines and their heterocyclic aza analogs were considered, and classification according to the method of ring formation was proposed.

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Section: -92%mentioning

confidence: 99%

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Platonova

Глухарева

Zimovets

et al. 2013

Chem Heterocycl Comp

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“…The conversion of 3,3-dimethylindoline-derived allene 58 to the corresponding tetracyclic azepine derivative 59 is an illustrative example (Scheme 12). [29] Scheme 12.…”

Section: Vinyl Azomethine Ylides and Butadienyl Azomethine Ylidesmentioning

confidence: 99%

Conjugated Azomethine Ylides

Melo

2006

Eur J Org Chem

148

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“…Brought to you by | Purdue University Libraries Authenticated Download Date | 5/30/15 5:54 AM A number of chemical reactions have been performed with propyne iminium salts 1 [4,5,8,[21][22][23][24][25][26][27][28][29][30][31][32][33][34]. In contrast, only few reactions of propiolamidinium salts 3 are known.…”

Section: Introductionmentioning

confidence: 99%

Orthoamides and iminium salts, LXXXIX. Reactions of N,N,N′,N′,N″,N″,N′″,N′″-octamethyl-acetylene-bis(carboxamidinium) tetrafluoroborate with nucleophilic reagents – new methods for the preparation of amidinium salts and ketene aminalsa

Drandarov

Tiritiris

Kantlehner³

2015

Zeitschrift Für Naturforschung B

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The acetylene-bis(carboxamidinium) salt 4 dehydrates carboxylic acids to the corresponding anhydrides, as the byproduct 2-oxo-but-2-en-amidinium salt 6b was isolated. Aromatic hydroxy compounds and 2-furyl-methylmercaptan add to the triple bond of the salt 4 to give 2-aryloxy-and 2-alkylmercapto-but-2-enebis(amidinium) salts 7-9. According to this reaction principle, 2-organoamino-buten-2-ene-bis(amidinium) salts 10 and 11 were prepared from 4 and primary and secondary amines, whereas 4-chlorobenzhydrazide reacted with 4 to give the imidazole-3-carboxamidinium salt 13. The reaction of CH 2 -acidic compounds as malononitrile or ethyl cyanoacetate with the bis(amidinium) salt 4 affords 2-cyanomethylene-but-3-enamidinium salts 15. With the CH-acidic diethyl 2-bromomalonate, compound 4 undergoes a Michael-initiated ring closure cyclopropenation reaction with further ring opening by the released Br -to the corresponding 2-diethoxycarbonylmethylene-3-bromo-but-3-enamidinium salt 18. Unlike cyclopentadiene and furane, the reaction of N-methylpyrrole and bis(amidinium) salt 4 does not lead to Diels-Alder [4 + 2] cycloadduct but to the Michaeltype 1:1 adduct 20. Pyrrole-and thiophene-2-carboxamidinium salts 23-25 can be prepared from compound 4 and esters of glycine, N-methylglycine (sarcosine), and mercaptoacetic acid, respectively. The derivatives of quinoxaline-2-carboxamidinium salts 29 are accessible from aromatic 1,2-diamines and compound 4. The reaction of the CH 2 /NH-acidic cyanoacetamide with the bis(amidinium) salt 4 produced the 3-pyrroline-2-on derivatives 33.

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Tri- and Tetracyclic Azepine Derivatives by Thermally Induced Cyclization of Aminoallenes and Semicyclic 2-Dienamines

Cited by 40 publications

References 24 publications

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Conjugated Azomethine Ylides

Orthoamides and iminium salts, LXXXIX. Reactions of N,N,N′,N′,N″,N″,N′″,N′″-octamethyl-acetylene-bis(carboxamidinium) tetrafluoroborate with nucleophilic reagents – new methods for the preparation of amidinium salts and ketene aminalsa

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