Home / Publications / One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine

One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine

Valentin Dmitrievich Gvozdev 1
Valentin Dmitrievich Gvozdev
, 
Konstantin Nikolaevich Shavrin 1
Konstantin Nikolaevich Shavrin
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
, 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
10.1016/j.mencom.2015.09.002
Published 2015-09-10
Communication , Volume 25, Issue 5, 329-331
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Gvozdev V. D. et al. One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine // Mendeleev Communications. 2015. Vol. 25. No. 5. pp. 329-331.
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Gvozdev V. D., Shavrin K. N., Egorov M. P., Nefedov O. M. One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine // Mendeleev Communications. 2015. Vol. 25. No. 5. pp. 329-331.
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TY - JOUR
DO - 10.1016/j.mencom.2015.09.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.09.002
TI - One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine
T2 - Mendeleev Communications
AU - Gvozdev, Valentin Dmitrievich
AU - Shavrin, Konstantin Nikolaevich
AU - Egorov, Mikhail Petrovich
AU - Nefedov, Oleg Matveevich
PY - 2015
DA - 2015/09/10
PB - Mendeleev Communications
SP - 329-331
IS - 5
VL - 25
ER -
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@article{2015_Gvozdev,
author = {Valentin Dmitrievich Gvozdev and Konstantin Nikolaevich Shavrin and Mikhail Petrovich Egorov and Oleg Matveevich Nefedov},
title = {One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.09.002},
number = {5},
pages = {329--331},
doi = {10.1016/j.mencom.2015.09.002}
}
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Gvozdev, Valentin Dmitrievich, et al. “One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine.” Mendeleev Communications, vol. 25, no. 5, Sep. 2015, pp. 329-331. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.09.002.

Abstract

Cyclization of 5-arylalk-4-ynals with o-aminobenzylamine or o-aminobenzyl alcohol in DMSO under the sequential action of NH4Br and KOH affords (E)-1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinazolines or (E)-1-arylmethylidene-1,2,3,3a-tetrahydro- 5H-pyrrolo-[1,2-a][3,1]benzoxazines; the latter without substituents in the 3-position easily isomerize into the corresponding 2-arylmethyl- 1-(2-hydroxymethylphenyl)pyrroles.

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