Preparation and novel reduction reactions of vinamidinium salts

I. W. Davies; M. Taylor; J. F. Marcoux; J. Wu; P. G. Dormer; D. Hughes; P. J. Reider

doi:10.1021/jo005656p

Preparation and novel reduction reactions of vinamidinium salts

I. W. Davies, M. Taylor, J. F. Marcoux, J. Wu, P. G. Dormer, D. Hughes, P. J. Reider

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32 Scopus citations

Abstract

Substituted acetic acids and formamides react in the presence of phosphorus oxychloride to yield the vinamidinium hexafluorophosphate salts 5a-d, 6a-d, and 7 in moderate to good unoptimized recrystallized yields, (40-67%) as easily handled nonhygroscopic solids. The 1,3-differentially substituted vinamidinium salts 8 was prepared by amine exchange in 81% yield as are the cyclic diazapinium salts 9 and 19 in >76% yield. The symmetrical 2-chlorovinamidinium 11 was prepared by displacement of 3 in 71% yield. The 2-chlorovinamidinium salts are cleanly reduced to the parent vinamidinium salts 12-16 using HI or PPh₃/pTSA in up to 99% assay yield.

Original language	English (US)
Pages (from-to)	251-255
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	66
Issue number	1
DOIs	https://doi.org/10.1021/jo005656p
State	Published - Jan 12 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo005656p

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title = "Preparation and novel reduction reactions of vinamidinium salts",

abstract = "Substituted acetic acids and formamides react in the presence of phosphorus oxychloride to yield the vinamidinium hexafluorophosphate salts 5a-d, 6a-d, and 7 in moderate to good unoptimized recrystallized yields, (40-67\%) as easily handled nonhygroscopic solids. The 1,3-differentially substituted vinamidinium salts 8 was prepared by amine exchange in 81\% yield as are the cyclic diazapinium salts 9 and 19 in >76\% yield. The symmetrical 2-chlorovinamidinium 11 was prepared by displacement of 3 in 71\% yield. The 2-chlorovinamidinium salts are cleanly reduced to the parent vinamidinium salts 12-16 using HI or PPh3/pTSA in up to 99\% assay yield.",

author = "Davies, \{I. W.\} and M. Taylor and Marcoux, \{J. F.\} and J. Wu and Dormer, \{P. G.\} and D. Hughes and Reider, \{P. J.\}",

year = "2001",

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doi = "10.1021/jo005656p",

language = "English (US)",

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journal = "Journal of Organic Chemistry",

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T1 - Preparation and novel reduction reactions of vinamidinium salts

AU - Davies, I. W.

AU - Taylor, M.

AU - Marcoux, J. F.

AU - Wu, J.

AU - Dormer, P. G.

AU - Hughes, D.

AU - Reider, P. J.

PY - 2001/1/12

Y1 - 2001/1/12

N2 - Substituted acetic acids and formamides react in the presence of phosphorus oxychloride to yield the vinamidinium hexafluorophosphate salts 5a-d, 6a-d, and 7 in moderate to good unoptimized recrystallized yields, (40-67%) as easily handled nonhygroscopic solids. The 1,3-differentially substituted vinamidinium salts 8 was prepared by amine exchange in 81% yield as are the cyclic diazapinium salts 9 and 19 in >76% yield. The symmetrical 2-chlorovinamidinium 11 was prepared by displacement of 3 in 71% yield. The 2-chlorovinamidinium salts are cleanly reduced to the parent vinamidinium salts 12-16 using HI or PPh3/pTSA in up to 99% assay yield.

AB - Substituted acetic acids and formamides react in the presence of phosphorus oxychloride to yield the vinamidinium hexafluorophosphate salts 5a-d, 6a-d, and 7 in moderate to good unoptimized recrystallized yields, (40-67%) as easily handled nonhygroscopic solids. The 1,3-differentially substituted vinamidinium salts 8 was prepared by amine exchange in 81% yield as are the cyclic diazapinium salts 9 and 19 in >76% yield. The symmetrical 2-chlorovinamidinium 11 was prepared by displacement of 3 in 71% yield. The 2-chlorovinamidinium salts are cleanly reduced to the parent vinamidinium salts 12-16 using HI or PPh3/pTSA in up to 99% assay yield.

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Preparation and novel reduction reactions of vinamidinium salts

Abstract

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