The Synthesis of 4-Nitro-, 5-Nitro-, 6-Nitro- and 7-Nitroindole<sup>1</sup>

Parmerter, Stanley M.; Cook, A. Gilbert; Dixon, William B.

doi:10.1021/ja01550a052

Cited by 45 publications

(16 citation statements)

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“…Alternatively we prepared 6 from o-nitroaniline or from ethyl 7-nitroindole 2-carboxylate (ACROS) by described procedures. [29,30] Analytical TLC was performed on 0.25 mm silica 60 coated aluminum foils with F 254 indicator (Merck). Preparative column chromatography was executed using silica gel (Merck 60, 0.063 ± 0.200 mm).…”

Section: Methodsmentioning

confidence: 99%

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

et al. 2000

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On the basis of molecular modeling studies, the 7-nitroindole nucleoside 1 was selected as a suitable photochemical precursor for photochemical generation of the C1' deoxyribosyl radical under irradiation, which led to 2'-deoxyribonolactone. The nitro-indole nucleoside derivatives 1a and 1b were prepared and their conformation was determined by X-ray crystallography and NMR spectroscopy. The photoreaction of these nucleosides gave the corresponding deoxyribonolactone derivatives efficiently, with release of 7-nitrosoindole. This reaction was successfully applied to synthesis of oligonucleotides containing the deoxyribonolactone lesion.

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Section: Methodsmentioning

confidence: 99%

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

et al. 2000

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“…Phenylhydrazones represent the principal starting material in the synthesis of indole derivatives. Some works have reported the synthesis of indole derivatives from the mixture of the two tautomers of phenylhydrazone without separation (Parmerter et al, 1958;Murakami et al, 1999;Narayana et al, 2005;El Kihel et al, 2013). Among these, Murakami et al (1999) reported the separation of the mixture of indole normal and indole abnormal.…”

Section: Structure Descriptionmentioning

confidence: 99%

Ethyl 2-[(Z)-2-(2-nitrophenyl)hydrazinylidene]propanoate

et al. 2016

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“…For related structures, see: Hu et al (2005); Harrison et al (2006); Butcher et al (2006). For background, see: Murphy et al (1997); Cavallini et al (1958); Robinson (1969Robinson ( , 1982; Hughes (1993); Murakami (1999); Narayana et al (2005Narayana et al ( , 2006; Singer & Shive (1957); Parmerter et al (1958). V = 920.0 (15) Å 3 Z = 4 Mo K radiation = 4.44 mm À1 T = 103 K 0.50 Â 0.08 Â 0.04 mm…”

Section: Related Literaturementioning

confidence: 99%

Methyl 5-bromo-1H-indole-2-carboxylate

et al. 2007

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Key indicators: single-crystal X-ray study; T = 103 K; mean (C-C) = 0.009 Å; R factor = 0.063; wR factor = 0.145; data-to-parameter ratio = 18.3. The indole ring system in the title compound, C 10 H 8 BrNO 2 , is planar. The sum of the angles around the indole N atom (359.9 ) indicates sp 2 -hybridization. The carboxylate group adopts a planar arrangement with respect to the indole ring system. The crystal structure is stabilized by intermolecular hydrogen-bond interactions. ExperimentalCrystal data C 10 H 8 BrNO 2 M r = 254.08 Monoclinic, P2 1 =n a = 12.911 (12) Å b = 3.907 (3) Å c = 18.923 (18) Å = 105.460 (14) V = 920.0 (15) Å 3 Z = 4 Mo K radiation = 4.44 mm À1 T = 103 K 0.50 Â 0.08 Â 0.04 mm Data collection Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T min = 0.215, T max = 0.843 6377 measured reflections 2339 independent reflections 1432 reflections with I > 2(I) R int = 0.071

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The Synthesis of 4-Nitro-, 5-Nitro-, 6-Nitro- and 7-Nitroindole¹

Cited by 45 publications

References 2 publications

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

Ethyl 2-[(Z)-2-(2-nitrophenyl)hydrazinylidene]propanoate

Methyl 5-bromo-1H-indole-2-carboxylate

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The Synthesis of 4-Nitro-, 5-Nitro-, 6-Nitro- and 7-Nitroindole1

Cited by 45 publications

References 2 publications

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

The 7-Nitroindole Nucleoside as a Photochemical Precursor of 2′-Deoxyribonolactone: Access to DNA Fragments Containing This Oxidative Abasic Lesion

Ethyl 2-[(Z)-2-(2-nitrophenyl)hydrazinylidene]propanoate

Methyl 5-bromo-1H-indole-2-carboxylate

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The Synthesis of 4-Nitro-, 5-Nitro-, 6-Nitro- and 7-Nitroindole¹