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(2 + 2)-Cycloaddition of o-quinones to N,N-dialkyl-3-alken-1-ynyl-1-amines. Thermal or photochemical ring closure of the adducts to 2H-1-benzopyran derivatives

✍ Scribed by W. Verboom; A. V. E. George; L. Brandsma; H. J. T. Bos

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 394 KB
Volume: 99
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19800990109

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✦ Synopsis

Abstract

Addition of 9,10‐phenanthrenequinone or 3,5‐di‐tert‐butyl‐o‐benzoquinone to N,N‐dialkyl‐3‐alken‐1‐ynyl‐1‐amines R^2^‐CHCH‐C≡C‐NR^1^~2~ (4) gives quinoid α‐alkenyl‐γ‐oxo‐α,β‐unsaturated carboxamides 6 or 8, respectively; these undergo a spontaneous ring‐closure, or can be cyclised photochemically into 2__H__‐phenanthro[9,10‐b]pyran‐4‐carboxamides 7 or 2__H__‐1‐benzopyran‐4‐carboxamides 9.

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