Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine

Matthew T. Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel

doi:10.1055/s-0033-1338852

Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine

Matthew T. Richers
, Indubhusan Deb
, Alena Yu Platonova
, Chen Zhang
, Daniel Seidel

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

69 Scopus citations

Abstract

Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine α-amination/N-alkylation. This unique α-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.

Original language	English
Article number	SS-2013-C0210-FA
Pages (from-to)	1730-1748
Number of pages	19
Journal	Synthesis (Germany)
Volume	45
Issue number	13
DOIs	https://doi.org/10.1055/s-0033-1338852
State	Published - 2013
Externally published	Yes

Keywords

C-H bond functionalization
Friedländer condensation
aminals
quinazolinone alkaloids
redox isomerization

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10.1055/s-0033-1338852

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Richers, M. T., Deb, I., Platonova, A. Y., Zhang, C., & Seidel, D. (2013). Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine. Synthesis (Germany), 45(13), 1730-1748. Article SS-2013-C0210-FA. https://doi.org/10.1055/s-0033-1338852

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title = "Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine",

abstract = "Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine α-amination/N-alkylation. This unique α-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.",

keywords = "C-H bond functionalization, Friedl{\"a}nder condensation, aminals, quinazolinone alkaloids, redox isomerization",

author = "Richers, \{Matthew T.\} and Indubhusan Deb and Platonova, \{Alena Yu\} and Chen Zhang and Daniel Seidel",

year = "2013",

doi = "10.1055/s-0033-1338852",

language = "English",

volume = "45",

pages = "1730--1748",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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}

Richers, MT, Deb, I, Platonova, AY, Zhang, C & Seidel, D 2013, 'Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine', Synthesis (Germany), vol. 45, no. 13, SS-2013-C0210-FA, pp. 1730-1748. https://doi.org/10.1055/s-0033-1338852

Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine. / Richers, Matthew T.; Deb, Indubhusan; Platonova, Alena Yu et al.
In: Synthesis (Germany), Vol. 45, No. 13, SS-2013-C0210-FA, 2013, p. 1730-1748.

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

TY - JOUR

T1 - Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes

T2 - Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine

AU - Richers, Matthew T.

AU - Deb, Indubhusan

AU - Platonova, Alena Yu

AU - Zhang, Chen

AU - Seidel, Daniel

PY - 2013

Y1 - 2013

N2 - Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine α-amination/N-alkylation. This unique α-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.

AB - Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine α-amination/N-alkylation. This unique α-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.

KW - C-H bond functionalization

KW - Friedländer condensation

KW - aminals

KW - quinazolinone alkaloids

KW - redox isomerization

UR - https://www.scopus.com/pages/publications/84879507345

U2 - 10.1055/s-0033-1338852

DO - 10.1055/s-0033-1338852

M3 - Article

AN - SCOPUS:84879507345

SN - 0039-7881

VL - 45

SP - 1730

EP - 1748

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 13

M1 - SS-2013-C0210-FA

ER -

Facile access to ring-fused aminals via direct α-amination of secondary amines with o-aminobenzaldehydes: Synthesis of vasicine, deoxyvasicine, deoxyvasicinone, mackinazolinone, and ruteacarpine

Abstract

Keywords

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