Internal Addition of Ketocarbenes to Conjugated Double Bonds

Becker, D.; Loewenthal, H. J. E.

doi:10.1002/ijch.197200040

Cited by 11 publications

(4 citation statements)

References 28 publications

(18 reference statements)

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“…N-Methyl-4-[jV-methyl-4-(N-methyl-4-nitropyrrole-2carboxamide)pyrrole-2-carboxamido]pyrrole-2-carboxamido-/?-methylpropionitrile (5). This nitrile was obtained from acid 2 and /3-aminobutyronitrile (18) as described for the acetonitrile homologue 3: 76% yield; mp 240 °C; NMR 5 1.4 (CH3, d, J = 6 Hz), 2.72 (2 H), 3.88, 3.92, 4.02 (N-CH3 groups), 7.08, 7.12, 7.23, 7.3, 7.69, 8.12 (aromatic H's), 8.01, 9.84,10.12 (amide H's); UV Xmal (DMF) 295 nm (e 27700); IR Vma 3300-3600,1660, 1650, 1300; MS m/e 480 (M+, 19), 441 (3.7), 413 (15), 370 (10), 275 (100). Anal.…”

Section: Methodsmentioning

confidence: 99%

“…The synthetic route followed was identical with the one described in type a. The appropriate aminobenzonitrile was used in the condensation reaction with the acid 2 to give, after further reactions parallel to the ones described above (Scheme I), the required p-( 14),12a m- (15), and o-aminobenzamidine (16).…”

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confidence: 99%

“…Previous studies showed that distamycin A inhibits the replication of HSV in cultured cells. 15 The present investigation was done using four different techniques: (1) Toxicity of the different compounds to growing cells. Only nontoxic compounds or toxic compounds at nontoxic concentrations were further tested.…”

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confidence: 99%

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Structure-activity relationships of pyrroleamidine antiviral antibiotics. 1. Modifications of the alkylamidine side chain

Bialer¹,

Yagen²,

Mechoulam³

et al. 1979

J. Med. Chem.

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Representatives of three types of side-chain analogues of distamycin A (1) were synthesized. These were tested for cytotoxicity, inhibition of herpes simplex virus (HSV) replication in cultured cells, effects on the synthesis of HSV DNA in isolated nuclei in vitro, as well as on DNA synthesis by purified HSV DNA polymerase. Distamycin A was the most active compound in all three antiviral tests, as well as the most toxic. However, several compounds, in particular the aromatic analogues 15 and 16, showed no toxicity under the experimental conditions used but were still very active in the three antiviral tests.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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Structure-activity relationships of pyrroleamidine antiviral antibiotics. 1. Modifications of the alkylamidine side chain

Bialer¹,

Yagen²,

Mechoulam³

et al. 1979

J. Med. Chem.

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“…(c) The monopeptide homologue of congocidine (16) was prepared from the known nitro amidine (14)24 in a way similar to that described previously (Scheme II). The nitro amidine (14)24 was catalytically reduced to the amino amidine (15), which was reacted with glycocyamine hydrochloride (13) in the presence of DCC (Scheme II), giving the desired congocidine.…”

mentioning

confidence: 99%

Structure-activity relationships of pyrrole amidine antiviral antibiotics. 2. Preparation of mono- and tripyrrole derivatives of congocidine

Bialer¹,

Yagen²,

Mechoulam³

et al. 1980

J. Med. Chem.

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Representatives of three types of congocidine (1) analogues were synthesized. These were tested for cytotoxicity, inhibition of herpes simplex virus (HSV) replication in cultured cells, and effects on the synthesis of HS DNA in isolated nuclei in vitro, as well as on DNA synthesis by purified HSV DNA polymerase. All synthesized tripyrrole derivatives of congocidine were less cytotoxic and more active than the parent drug in all the three ant iviral tests.

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Intramolecular Reactions of Diazocarbonyl Compounds

Burke

Grieco

1979

Organic Reactions

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Since the demonstration by Stork and Ficini in 1961 that unsaturated diazoketones undergo intramolecular cyclization to form cyclopropanes the intramolecular reactions of α‐diazocarbonyl compounds have been extensively studied under thermal, catalytic, and photochemical conditions. Intramolecular cyclization of α‐carbonyl carbenes and carbenoids has found widespread application to the synthesis of theoretically interesting compounds such as bullvalene, twistane, bridged annulenes, and barbaralone, as well as syntheses of natural products such as sabinene, sirenin, α‐chamigrene, and phyllocladene. The reaction has also allowed the construction of several intriguing polycyclic systems that were unattainable by alternative methods. A recent review has covered the reactions of diazoacetic esters with alkenes, alkynes, heterocyclics, and aromatic compounds. Unsaturated alkoxycarbonyl carbenes (:CHCO 2 R) and unsaturated carbonyl carbenes (:CHCOR) (where R contains either aromatic or olefinic groups), which are considered to be intermediates in the absence of catalyst, have been the subject of several other reviews. A review concerning photochemically, thermally, and catalytically induced Wolff rearrangements of α‐diazocarbonyl compounds has recently appeared. However to date no comprehensive review has appeared which demonstrates the synthetic potential of α‐diazocarbonyl insertion and addition reactions. In reviewing the reactions of α‐diazocarbonyl compounds chosen not to include certain peripheral topics such as intermolecular reactions, intramolecular dimerization of bis(α‐carbonyl carbenoids) to give diacyl cycloolefins and intramolecular trimerizations of tris(α‐keto carbenoids), affording triacylcyclopropanes are not included. Also excluded are base‐catalyzed reactions of α‐diazocarbonyl compounds and certain ring‐contraction reactions involving CC bond insertion of intermediate α‐ketocarbenes. The topics included in this report are the intramolecular reactions of α‐carbonyl carbenes and carbenoids with olefinic and aromatic unsaturation, with CH bonds, and with CC and NH single bonds. Also included are acid‐catalyzed cyclization reactions of α‐diazoketones.

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Internal Addition of Ketocarbenes to Conjugated Double Bonds

Cited by 11 publications

References 28 publications

Structure-activity relationships of pyrroleamidine antiviral antibiotics. 1. Modifications of the alkylamidine side chain

Structure-activity relationships of pyrroleamidine antiviral antibiotics. 1. Modifications of the alkylamidine side chain

Structure-activity relationships of pyrrole amidine antiviral antibiotics. 2. Preparation of mono- and tripyrrole derivatives of congocidine

Intramolecular Reactions of Diazocarbonyl Compounds

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