ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Heterocyclic β-Enamino Esters, 12. The Synthesis of Benzo[b]furo[2′,3′-e][l,4]diazepines and Furo[2,3-b][1,5]diazocines and of α-Heterocyclically Substituted γ-Lactones from Ethyl 2-Amino-4,5-dihydro-3-furanecarboxylatesThe ethyl 2-amino-4,5-dihydro-3-furanecarboxylates 1a-d react with 1,2-diaminocyclo-hexane and 1,3-diaminopropane to form the ring systems of benzo[b] furo[2′,3′-e][1,4] diazepines 2a-c and furo[2,3-b][1,5]diazicines 3a-c, respectively. With o-phenylenediamine, 1,8-diaminonaphthalene, 2-aminophenol, and 2-aminoethanol one obtains after ring cleavage and subsequent lactonization α-(2-benzimidazlyl)- (8a, b), α-(2-perimidinyl)-(6a, b), α-(2-benzoxazolyl)- (13a, b), and α-(2-oxazolin-2-yl)-γ-Iactones (15a, b). I. r. and n. m. r. data are discussed.
Notes:
Die 2-Amino-4.5-dihydro-3-furancarbonsäure-äthylester 1a-d reagieren mit 1,2-Diaminocyclohexan und 1,3-Diaminopropan zu den Ringgerüsten der Benzo[b] furo[2′,3′-e][1,4]-diazepine 2a-c und Furo[2,3- b][1,5]diazocine 3a-c. Mit o-Phenylendiamin. 1,8-Diaminonaphthalin, 2-Aminophenol und 2- Aminoäthanol erhält man nach Ringöffnung und Lactonisierung die α-(2-Benzimidazoly)- (8a, b), α-(2-Perimidinyl)- (6a, b) α-(2-Benzoxazolyl)-(13a, b) und α-(2-Oxazolin-2-yl)-γ-lactone (15a, b) Die IR- und NMR-Daten werden diskutiert.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19741070605
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