Nitrogen bridgehead compounds. Part 41. Ring transformation of nitrogen bridgehead ring systems

I. Hermecz, Zoltán Mészáros, Kálmán Simon, László Szabó, Zoltán Pál

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

In an investigation of the role of the nitrogen atoms in the ring-transformation reactions of nitrogen bridgehead condensed pyrimidinones (1), either the bridgehead or the non-bridgehead nitrogen atom was replaced by a carbon atom. While replacement of the non-bridgehead nitrogen atom did not influence the ring-transformation reaction, replacement of the bridgehead nitrogen atom prevented the rearrangement. Thus, ethyl 1-cyano-6-methyl-4-oxp- 4H-quinolizine-3-carboxylate (10) was transformed into ethyl 8-cyano-5-hydroxy-2-methylquinoline-6-carboxylate (11) at 250 °C. X-Ray crystallographic analysis confirms the structure of (11): monoclinic system with a = 11.385(1), b = 11.102(1), c = 10.191(2)Å, space group P2 1/n, Z = 4, Dc = 1.36 g cm-3, R = 0.043. The quinoline (11) gave 5-ethoxy-2-methylquinoline-8-nitrile (12) at 260 °C.

Original languageEnglish
Pages (from-to)1795-1798
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1984

Fingerprint

Nitrogen Compounds
Nitrogen
Atoms
Quinolizines
Pyrimidinones
Nitriles
Carbon
X rays

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Nitrogen bridgehead compounds. Part 41. Ring transformation of nitrogen bridgehead ring systems. / Hermecz, I.; Mészáros, Zoltán; Simon, Kálmán; Szabó, László; Pál, Zoltán.

In: Journal of the Chemical Society, Perkin Transactions 1, 1984, p. 1795-1798.

Research output: Contribution to journalArticle

Hermecz, I. ; Mészáros, Zoltán ; Simon, Kálmán ; Szabó, László ; Pál, Zoltán. / Nitrogen bridgehead compounds. Part 41. Ring transformation of nitrogen bridgehead ring systems. In: Journal of the Chemical Society, Perkin Transactions 1. 1984 ; pp. 1795-1798.
@article{fa52139d752a447d8de3644eb855ce23,
title = "Nitrogen bridgehead compounds. Part 41. Ring transformation of nitrogen bridgehead ring systems",
abstract = "In an investigation of the role of the nitrogen atoms in the ring-transformation reactions of nitrogen bridgehead condensed pyrimidinones (1), either the bridgehead or the non-bridgehead nitrogen atom was replaced by a carbon atom. While replacement of the non-bridgehead nitrogen atom did not influence the ring-transformation reaction, replacement of the bridgehead nitrogen atom prevented the rearrangement. Thus, ethyl 1-cyano-6-methyl-4-oxp- 4H-quinolizine-3-carboxylate (10) was transformed into ethyl 8-cyano-5-hydroxy-2-methylquinoline-6-carboxylate (11) at 250 °C. X-Ray crystallographic analysis confirms the structure of (11): monoclinic system with a = 11.385(1), b = 11.102(1), c = 10.191(2){\AA}, space group P2 1/n, Z = 4, Dc = 1.36 g cm-3, R = 0.043. The quinoline (11) gave 5-ethoxy-2-methylquinoline-8-nitrile (12) at 260 °C.",
author = "I. Hermecz and Zolt{\'a}n M{\'e}sz{\'a}ros and K{\'a}lm{\'a}n Simon and L{\'a}szl{\'o} Szab{\'o} and Zolt{\'a}n P{\'a}l",
year = "1984",
language = "English",
pages = "1795--1798",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",

}

TY - JOUR

T1 - Nitrogen bridgehead compounds. Part 41. Ring transformation of nitrogen bridgehead ring systems

AU - Hermecz, I.

AU - Mészáros, Zoltán

AU - Simon, Kálmán

AU - Szabó, László

AU - Pál, Zoltán

PY - 1984

Y1 - 1984

N2 - In an investigation of the role of the nitrogen atoms in the ring-transformation reactions of nitrogen bridgehead condensed pyrimidinones (1), either the bridgehead or the non-bridgehead nitrogen atom was replaced by a carbon atom. While replacement of the non-bridgehead nitrogen atom did not influence the ring-transformation reaction, replacement of the bridgehead nitrogen atom prevented the rearrangement. Thus, ethyl 1-cyano-6-methyl-4-oxp- 4H-quinolizine-3-carboxylate (10) was transformed into ethyl 8-cyano-5-hydroxy-2-methylquinoline-6-carboxylate (11) at 250 °C. X-Ray crystallographic analysis confirms the structure of (11): monoclinic system with a = 11.385(1), b = 11.102(1), c = 10.191(2)Å, space group P2 1/n, Z = 4, Dc = 1.36 g cm-3, R = 0.043. The quinoline (11) gave 5-ethoxy-2-methylquinoline-8-nitrile (12) at 260 °C.

AB - In an investigation of the role of the nitrogen atoms in the ring-transformation reactions of nitrogen bridgehead condensed pyrimidinones (1), either the bridgehead or the non-bridgehead nitrogen atom was replaced by a carbon atom. While replacement of the non-bridgehead nitrogen atom did not influence the ring-transformation reaction, replacement of the bridgehead nitrogen atom prevented the rearrangement. Thus, ethyl 1-cyano-6-methyl-4-oxp- 4H-quinolizine-3-carboxylate (10) was transformed into ethyl 8-cyano-5-hydroxy-2-methylquinoline-6-carboxylate (11) at 250 °C. X-Ray crystallographic analysis confirms the structure of (11): monoclinic system with a = 11.385(1), b = 11.102(1), c = 10.191(2)Å, space group P2 1/n, Z = 4, Dc = 1.36 g cm-3, R = 0.043. The quinoline (11) gave 5-ethoxy-2-methylquinoline-8-nitrile (12) at 260 °C.

UR - http://www.scopus.com/inward/record.url?scp=37049096582&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049096582&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:37049096582

SP - 1795

EP - 1798

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

ER -