Studies on 2-(α-Hydroxybenzyl)benzimidazole (HBB) Analogs. I. Synthesis of 8-(α-Hydroxybenzyl)purines, the Diaza Analogs of HBB<sup>1a,b</sup>

Haggerty, William J.; Springer, Robert H.; Cheng, C. C.

doi:10.1021/jm00330a015

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1970

1975

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Cited by 6 publications

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“…The naturally occurring halogenated pyrroles 1-5 have all yielded to synthesis. [1][2][3][4][5][6][7][8][9] All of these materials possess antibacterial properties of potential interest in human chemotherapy. We have prepared variations of pyoluteorin structure 1 and have examined them for in vitro and in vivo activity against a variety of pathogens and for antimalarial activity in mice.…”

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confidence: 99%

Antiviral. 1. 2-(.alpha.-Hydroxybenzyl)imidazo[4,5-c]pyridine

Berner¹,

Reinshagen²,

Koch³

1973

J. Med. Chem.

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confidence: 99%

Antiviral. 1. 2-(.alpha.-Hydroxybenzyl)imidazo[4,5-c]pyridine

Berner¹,

Reinshagen²,

Koch³

1973

J. Med. Chem.

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Syntheses from Pyrimidines

1971

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Coupling of 4,5-diiodophthalonitrile with rerr-butyldimethylsilylacetylene and a palladium catalyst gave 4,5-bis(rerr-butyldimethylsilylethynyl)phthalonitrile. Cleavage of the silyl moiety with tetftibutylammonium fluoride gave 4,5-diethynylphthalonitrile, while condensation in 2-N,N-dimethylami-noethanol without or with Zn(OAc)2 gave metal-free 2,3,8,9,16,17,23,24-wtakis(tert-butyldimethylsilylethy-nyl)phthalocyanine or its zinc derivative. Cleavage of the silyl groups of the zinc derivative gave an insoluble product whose tH NMR spectrum was indicative of 2,3,9,10,16,17,23,?A.-octaettrynylphthalocyaninato zinc(Il). Bromination of phthalonitrile withN,lV{ibromoisocyanuric acid gave a separable mixture of 3,6-,3,21-and 4,S-dibromophthalonitrile along with the monobromophthalonitrites. Coupling of 3,4dibromophalonitrile with ren-butylacetylene gave 3,4-bis(ren-butylethynyl)phthalonitrile, which on condensation with lithium l-pentanolate gave 1,2,8,9,15,16,22,23-octzkjs(3,3-dimethyl-l-butynyl)phthalocyanins as a single isomer, the first known 1,2,8,9,15.16,22,23-octasubstituted phthalocyanine.

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The Oxo‐(Hydroxy‐) and Alkoxypurines

1971

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Studies on 2-(α-Hydroxybenzyl)benzimidazole (HBB) Analogs. I. Synthesis of 8-(α-Hydroxybenzyl)purines, the Diaza Analogs of HBB^1a,b

Cited by 6 publications

References 0 publications

Antiviral. 1. 2-(.alpha.-Hydroxybenzyl)imidazo[4,5-c]pyridine

Antiviral. 1. 2-(.alpha.-Hydroxybenzyl)imidazo[4,5-c]pyridine

Syntheses from Pyrimidines

The Oxo‐(Hydroxy‐) and Alkoxypurines

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Studies on 2-(α-Hydroxybenzyl)benzimidazole (HBB) Analogs. I. Synthesis of 8-(α-Hydroxybenzyl)purines, the Diaza Analogs of HBB1a,b

Cited by 6 publications

References 0 publications

Antiviral. 1. 2-(.alpha.-Hydroxybenzyl)imidazo[4,5-c]pyridine

Antiviral. 1. 2-(.alpha.-Hydroxybenzyl)imidazo[4,5-c]pyridine

Syntheses from Pyrimidines

The Oxo‐(Hydroxy‐) and Alkoxypurines

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Product

Resources

About

Studies on 2-(α-Hydroxybenzyl)benzimidazole (HBB) Analogs. I. Synthesis of 8-(α-Hydroxybenzyl)purines, the Diaza Analogs of HBB^1a,b