Simple and condensed β-lactams. Part 33. AlCl3 catalyzed ring closures of some 3-aryloxy-4-oxoazetidine-2-carboxylic chlorides to 1H-chromeno[3,2- b]azete-2,8(2aH,8aH)-diones and some reactions of the products

Ferenc Bertha, J. Fetter, M. Kajtár-Peredy, Károly Lempert

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Carboxylic chlorides 3a-3c, when treated with AlCl3, afforded the tricyclic compounds 17a-17c. NaBH4 reduction of 17a and 17b afforded compounds 11a and 11b. The latter and the related known compounds 4a, 5b, 6a and 7a were used for the preparation of various dihydrochromeno[3,2-b]azet- 2(1H)-ones and of a 3,4-disubstituted chromane-2-carboxylic ester (26) of fixed stereochemistry. Catalytic reduction of 8-chloro compound 5b afforded compounds 10b and 25, the products of simple hydrodechlorination and of azetidinone ring cleavage with concomitant hydrodechlorination, respectively.

Original languageEnglish
Pages (from-to)5567-5580
Number of pages14
JournalTetrahedron
Volume55
Issue number17
DOIs
Publication statusPublished - Apr 23 1999

Fingerprint

Lactams
Chlorides
Esters
Stereochemistry
aluminum chloride
2-azetidinone

Keywords

  • Azetidin-2-ones
  • Condensed chromanes
  • Diastereoselection
  • Ring cleavage

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Simple and condensed β-lactams. Part 33. AlCl3 catalyzed ring closures of some 3-aryloxy-4-oxoazetidine-2-carboxylic chlorides to 1H-chromeno[3,2- b]azete-2,8(2aH,8aH)-diones and some reactions of the products",
abstract = "Carboxylic chlorides 3a-3c, when treated with AlCl3, afforded the tricyclic compounds 17a-17c. NaBH4 reduction of 17a and 17b afforded compounds 11a and 11b. The latter and the related known compounds 4a, 5b, 6a and 7a were used for the preparation of various dihydrochromeno[3,2-b]azet- 2(1H)-ones and of a 3,4-disubstituted chromane-2-carboxylic ester (26) of fixed stereochemistry. Catalytic reduction of 8-chloro compound 5b afforded compounds 10b and 25, the products of simple hydrodechlorination and of azetidinone ring cleavage with concomitant hydrodechlorination, respectively.",
keywords = "Azetidin-2-ones, Condensed chromanes, Diastereoselection, Ring cleavage",
author = "Ferenc Bertha and J. Fetter and M. Kajt{\'a}r-Peredy and K{\'a}roly Lempert",
year = "1999",
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language = "English",
volume = "55",
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journal = "Tetrahedron",
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TY - JOUR

T1 - Simple and condensed β-lactams. Part 33. AlCl3 catalyzed ring closures of some 3-aryloxy-4-oxoazetidine-2-carboxylic chlorides to 1H-chromeno[3,2- b]azete-2,8(2aH,8aH)-diones and some reactions of the products

AU - Bertha, Ferenc

AU - Fetter, J.

AU - Kajtár-Peredy, M.

AU - Lempert, Károly

PY - 1999/4/23

Y1 - 1999/4/23

N2 - Carboxylic chlorides 3a-3c, when treated with AlCl3, afforded the tricyclic compounds 17a-17c. NaBH4 reduction of 17a and 17b afforded compounds 11a and 11b. The latter and the related known compounds 4a, 5b, 6a and 7a were used for the preparation of various dihydrochromeno[3,2-b]azet- 2(1H)-ones and of a 3,4-disubstituted chromane-2-carboxylic ester (26) of fixed stereochemistry. Catalytic reduction of 8-chloro compound 5b afforded compounds 10b and 25, the products of simple hydrodechlorination and of azetidinone ring cleavage with concomitant hydrodechlorination, respectively.

AB - Carboxylic chlorides 3a-3c, when treated with AlCl3, afforded the tricyclic compounds 17a-17c. NaBH4 reduction of 17a and 17b afforded compounds 11a and 11b. The latter and the related known compounds 4a, 5b, 6a and 7a were used for the preparation of various dihydrochromeno[3,2-b]azet- 2(1H)-ones and of a 3,4-disubstituted chromane-2-carboxylic ester (26) of fixed stereochemistry. Catalytic reduction of 8-chloro compound 5b afforded compounds 10b and 25, the products of simple hydrodechlorination and of azetidinone ring cleavage with concomitant hydrodechlorination, respectively.

KW - Azetidin-2-ones

KW - Condensed chromanes

KW - Diastereoselection

KW - Ring cleavage

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U2 - 10.1016/S0040-4020(99)00222-7

DO - 10.1016/S0040-4020(99)00222-7

M3 - Article

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VL - 55

SP - 5567

EP - 5580

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 17

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