Selective and simultaneous deprotection of amine and lactam functions in the syntheses of pyridazino[4,5-b]oxazinones and pyridazino[4,5-b]thiazinones

Erzsébet Zára-Kaczián, P. Mátyus

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Benzyloxymethyl (BOM) and benzyl (Bz) groups were employed for protection of the amide- and amino-nitrogens in the title compounds. The BOM protective group could be removed selectively or simultaneously with the Bz group depending on the reaction conditions. By catalytic hydrogenation of the fully protected pyridazinooxazinone (1b), unexpectedly the 4-methyl derivative (1e) could also be prepared. The mechanism for the formation of 1e is also discussed.

Original languageEnglish
Pages (from-to)519-528
Number of pages10
JournalHeterocycles
Volume36
Issue number3
Publication statusPublished - Mar 1 1993

Fingerprint

Lactams
Hydrogenation
Amides
Amines
Nitrogen
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Selective and simultaneous deprotection of amine and lactam functions in the syntheses of pyridazino[4,5-b]oxazinones and pyridazino[4,5-b]thiazinones. / Zára-Kaczián, Erzsébet; Mátyus, P.

In: Heterocycles, Vol. 36, No. 3, 01.03.1993, p. 519-528.

Research output: Contribution to journalArticle

@article{7d28a79b04e94fc0a66af5cdcedaf920,
title = "Selective and simultaneous deprotection of amine and lactam functions in the syntheses of pyridazino[4,5-b]oxazinones and pyridazino[4,5-b]thiazinones",
abstract = "Benzyloxymethyl (BOM) and benzyl (Bz) groups were employed for protection of the amide- and amino-nitrogens in the title compounds. The BOM protective group could be removed selectively or simultaneously with the Bz group depending on the reaction conditions. By catalytic hydrogenation of the fully protected pyridazinooxazinone (1b), unexpectedly the 4-methyl derivative (1e) could also be prepared. The mechanism for the formation of 1e is also discussed.",
author = "Erzs{\'e}bet Z{\'a}ra-Kaczi{\'a}n and P. M{\'a}tyus",
year = "1993",
month = "3",
day = "1",
language = "English",
volume = "36",
pages = "519--528",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "3",

}

TY - JOUR

T1 - Selective and simultaneous deprotection of amine and lactam functions in the syntheses of pyridazino[4,5-b]oxazinones and pyridazino[4,5-b]thiazinones

AU - Zára-Kaczián, Erzsébet

AU - Mátyus, P.

PY - 1993/3/1

Y1 - 1993/3/1

N2 - Benzyloxymethyl (BOM) and benzyl (Bz) groups were employed for protection of the amide- and amino-nitrogens in the title compounds. The BOM protective group could be removed selectively or simultaneously with the Bz group depending on the reaction conditions. By catalytic hydrogenation of the fully protected pyridazinooxazinone (1b), unexpectedly the 4-methyl derivative (1e) could also be prepared. The mechanism for the formation of 1e is also discussed.

AB - Benzyloxymethyl (BOM) and benzyl (Bz) groups were employed for protection of the amide- and amino-nitrogens in the title compounds. The BOM protective group could be removed selectively or simultaneously with the Bz group depending on the reaction conditions. By catalytic hydrogenation of the fully protected pyridazinooxazinone (1b), unexpectedly the 4-methyl derivative (1e) could also be prepared. The mechanism for the formation of 1e is also discussed.

UR - http://www.scopus.com/inward/record.url?scp=0007991565&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0007991565&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0007991565

VL - 36

SP - 519

EP - 528

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 3

ER -