Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino-[5,4-d]pyrimidines

A. Al-Azmi; B. L. Booth; R. A. Carpenter; A. Carvalho; E. Marrelec; R. G. Pritchard; M. Fernanda; J. R P Proença

doi:10.1039/b106539b

Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino-[5,4-d]pyrimidines

A. Al-Azmi, B. L. Booth, R. A. Carpenter, A. Carvalho, E. Marrelec, R. G. Pritchard, M. Fernanda, J. R P Proença

Research output: Contribution to journal › Article › peer-review

Abstract

6-Cyano-9-substituted-9H-purines were prepared in a high yielding, one-step process by refluxing triethyl orthoformate or triethyl orthopropionate with the corresponding (Z)-N1-(aryl- or benzyl)-N2-(2-amino-1,2-dicyanovinyl)formamidines. Attempted reaction of these cyanopurines with aqueous methylamine furnished 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines, by attack at the imidazole ring rather than addition to the 6-cyano group. All compounds have been fully characterised by spectroscopic data and an X-ray crystal structure determination has been carried out on the 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine.

Original language	English
Pages (from-to)	2532-2537
Number of pages	5
Journal	Journal of the Chemical Society. Perkin Transactions 1
Issue number	20
DOIs	https://doi.org/10.1039/b106539b
Publication status	Published - 2001

Keywords

Crystal structure; Molecular structure (of 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine); Ring enlargement (prepn. and ring-expansion of cyanopurines)

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10.1039/b106539b

CCDC 167808: Experimental Crystal Structure Determination
Al-Azmi, A. (Contributor), Booth, B. L. (Contributor), Carpenter, R. A. (Contributor), Carvalho, A. (Contributor), Marrelec, E. (Contributor), Pritchard, R. (Contributor) & Proença, J. R. P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2001
DOI: 10.5517/cc5mm5k, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc5mm5k&sid=DataCite
Dataset

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Al-Azmi, A., Booth, B. L., Carpenter, R. A., Carvalho, A., Marrelec, E., Pritchard, R. G., Fernanda, M., & Proença, J. R. P. (2001). Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino-[5,4-d]pyrimidines. Journal of the Chemical Society. Perkin Transactions 1, (20), 2532-2537. https://doi.org/10.1039/b106539b

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title = "Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino-[5,4-d]pyrimidines",

abstract = "6-Cyano-9-substituted-9H-purines were prepared in a high yielding, one-step process by refluxing triethyl orthoformate or triethyl orthopropionate with the corresponding (Z)-N1-(aryl- or benzyl)-N2-(2-amino-1,2-dicyanovinyl)formamidines. Attempted reaction of these cyanopurines with aqueous methylamine furnished 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines, by attack at the imidazole ring rather than addition to the 6-cyano group. All compounds have been fully characterised by spectroscopic data and an X-ray crystal structure determination has been carried out on the 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine.",

keywords = "Crystal structure; Molecular structure (of 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine); Ring enlargement (prepn. and ring-expansion of cyanopurines)",

author = "A. Al-Azmi and Booth, {B. L.} and Carpenter, {R. A.} and A. Carvalho and E. Marrelec and Pritchard, {R. G.} and M. Fernanda and Proen{\c c}a, {J. R P}",

year = "2001",

doi = "10.1039/b106539b",

language = "English",

pages = "2532--2537",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "20",

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TY - JOUR

T1 - Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino-[5,4-d]pyrimidines

AU - Al-Azmi, A.

AU - Booth, B. L.

AU - Carpenter, R. A.

AU - Carvalho, A.

AU - Marrelec, E.

AU - Pritchard, R. G.

AU - Fernanda, M.

AU - Proença, J. R P

PY - 2001

Y1 - 2001

N2 - 6-Cyano-9-substituted-9H-purines were prepared in a high yielding, one-step process by refluxing triethyl orthoformate or triethyl orthopropionate with the corresponding (Z)-N1-(aryl- or benzyl)-N2-(2-amino-1,2-dicyanovinyl)formamidines. Attempted reaction of these cyanopurines with aqueous methylamine furnished 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines, by attack at the imidazole ring rather than addition to the 6-cyano group. All compounds have been fully characterised by spectroscopic data and an X-ray crystal structure determination has been carried out on the 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine.

AB - 6-Cyano-9-substituted-9H-purines were prepared in a high yielding, one-step process by refluxing triethyl orthoformate or triethyl orthopropionate with the corresponding (Z)-N1-(aryl- or benzyl)-N2-(2-amino-1,2-dicyanovinyl)formamidines. Attempted reaction of these cyanopurines with aqueous methylamine furnished 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines, by attack at the imidazole ring rather than addition to the 6-cyano group. All compounds have been fully characterised by spectroscopic data and an X-ray crystal structure determination has been carried out on the 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine.

KW - Crystal structure; Molecular structure (of 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine); Ring enlargement (prepn. and ring-expansion of cyanopurines)

U2 - 10.1039/b106539b

DO - 10.1039/b106539b

M3 - Article

SN - 1472-7781

SP - 2532

EP - 2537

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 20

ER -

Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino-[5,4-d]pyrimidines

Abstract

Keywords

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Datasets

CCDC 167808: Experimental Crystal Structure Determination

Cite this